chore(deps)!: migrate from regexp2 v1 to regexp2 v2

Bumps [golang.org/x/sync](https://github.com/golang/sync) from 0.22.0 to 0.23.0.
- [Commits](https://github.com/golang/sync/compare/v0.22.0...v0.23.0)

---
updated-dependencies:
- dependency-name: golang.org/x/sync
  dependency-version: 0.23.0
  dependency-type: direct:production
  update-type: version-update:semver-minor
...

Signed-off-by: dependabot[bot] <support@github.com>
Co-authored-by: dependabot[bot] <49699333+dependabot[bot]@users.noreply.github.com>

.github/actions/build-test-push/action.yml

@@ -83,12 +83,16 @@ runs:
         INPUT_PLATFORM: ${{ inputs.platform }}
         INPUT_ALTERNATE_REPOSITORY: ${{ inputs.alternate_repository }}
         INPUT_DRY_RUN: ${{ inputs.dry_run }}
+        # Exporting the build cache needs a registry login. Forks run without
+        # credentials, so they import the cache but never export it.
+        INPUT_CACHE_WRITABLE: ${{ inputs.docker_hub_username != '' }}
       run: |
         .github/actions/build-test-push/build.sh \
           --version "$INPUT_VERSION" \
           --platform "$INPUT_PLATFORM" \
           --alternate-repository "$INPUT_ALTERNATE_REPOSITORY" \
-          --dry-run "$INPUT_DRY_RUN"
+          --dry-run "$INPUT_DRY_RUN" \
+          --cache-writable "$INPUT_CACHE_WRITABLE"
 
     - name: Run integration tests
       if: inputs.skip_integrations_tests != 'true'

.github/actions/build-test-push/build.sh

@@ -12,6 +12,7 @@ version=""
 platform=""
 alternate_repository=""
 dry_run=""
+cache_writable=""
 
 while [[ $# -gt 0 ]]; do
   case $1 in
@@ -31,6 +32,10 @@ while [[ $# -gt 0 ]]; do
       dry_run="$2"
       shift 2
       ;;
+    --cache-writable)
+      cache_writable="$2"
+      shift 2
+      ;;
     *)
       echo "Unknown option $1"
       exit 1
@@ -44,11 +49,41 @@ echo
 echo "Gotenberg version: $version"
 echo "Target platform: $platform"
 
+# The build cache lives under the canonical repository, captured before the
+# alternate-repository override below. Pull requests build into "snapshot", so
+# deriving the cache ref after the override would give them a cache namespace
+# of their own and they would never import what main published, which is the
+# population that benefits most.
+cache_image="$DOCKER_REGISTRY/$DOCKER_REPOSITORY"
+
+# Layers are per-architecture, so each platform keeps its own cache manifest.
+cache_platform="${platform//\//-}"
+
+# Layers running "apt-get upgrade" install whatever versions are current at
+# build time, and the packages are deliberately not pinned. A persistent cache
+# would turn those into hits and freeze security patches into a published
+# image until debian:13-slim itself changes digest. Keying them on the ISO week
+# bounds that staleness to seven days while leaving every build within a week
+# free to reuse the cache.
+apt_snapshot="$(date -u +%G-W%V)"
+
+# Only a build that is not redirected to an alternate repository writes the
+# cache, so a pull request cannot make its own state the baseline for main.
+# Reading stays enabled everywhere, including forks, since the cache ref is
+# public and needs no credentials.
+cache_to_enabled="false"
+if [ "$cache_writable" = "true" ] && [ -z "$alternate_repository" ]; then
+  cache_to_enabled="true"
+fi
+
 if [ -n "$alternate_repository" ]; then
   DOCKER_REPOSITORY=$alternate_repository
   echo "⚠️ Using $alternate_repository for DOCKER_REPOSITORY"
 fi
 
+echo "Build cache: $cache_image:buildcache-<target>-$cache_platform (write: $cache_to_enabled)"
+echo "APT snapshot: $apt_snapshot"
+
 if [ "$dry_run" = "true" ]; then
   echo "🚧 Dry run"
 fi
@@ -189,12 +224,36 @@ join() {
   echo "$*"
 }
 
+# cache_flags echoes the buildx cache arguments for a build target. Each target
+# keeps its own manifest so that the Chromium and LibreOffice variants, which
+# branch from common-stage rather than from each other, do not overwrite one
+# another's entry.
+#
+# mode=max exports intermediate stages too, not just the final layers, which is
+# what makes the expensive apt and jlink stages reusable. type=registry, not
+# type=gha: the GitHub Actions cache is capped at 10 GB per repository and is
+# already carrying the Go and golangci-lint caches that the lint and test jobs
+# depend on. Multi-GB image layers across five platforms would evict them.
+cache_flags() {
+  local target="$1"
+  local ref="$cache_image:buildcache-$target-$cache_platform"
+  local flags="--cache-from type=registry,ref=$ref"
+
+  if [ "$cache_to_enabled" = "true" ]; then
+    flags="$flags --cache-to type=registry,ref=$ref,mode=max"
+  fi
+
+  echo "$flags"
+}
+
 no_arch_tag="$DOCKER_REGISTRY/$DOCKER_REPOSITORY:$version"
 
 # Full variant.
 cmd="docker buildx build \
     --target gotenberg \
     --build-arg GOTENBERG_VERSION=$version \
+    --build-arg APT_SNAPSHOT=$apt_snapshot \
+    $(cache_flags gotenberg) \
     --platform $platform \
     --load \
     ${tags_flags[*]} \
@@ -207,6 +266,8 @@ run_cmd "$cmd"
 cmd="docker buildx build \
     --target gotenberg-chromium \
     --build-arg GOTENBERG_VERSION=$version \
+    --build-arg APT_SNAPSHOT=$apt_snapshot \
+    $(cache_flags gotenberg-chromium) \
     --platform $platform \
     --load \
     ${tags_chromium_flags[*]} \
@@ -218,6 +279,8 @@ run_cmd "$cmd"
 cmd="docker buildx build \
     --target gotenberg-libreoffice \
     --build-arg GOTENBERG_VERSION=$version \
+    --build-arg APT_SNAPSHOT=$apt_snapshot \
+    $(cache_flags gotenberg-libreoffice) \
     --platform $platform \
     --load \
     ${tags_libreoffice_flags[*]} \
@@ -230,6 +293,8 @@ if [ "$platform" = "linux/amd64" ]; then
   cmd="docker buildx build \
       --target gotenberg-cloudrun \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-cloudrun) \
       --platform $platform \
       --load \
       ${tags_cloud_run_flags[*]} \
@@ -240,6 +305,8 @@ if [ "$platform" = "linux/amd64" ]; then
   cmd="docker buildx build \
       --target gotenberg-cloudrun-chromium \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-cloudrun-chromium) \
       --platform $platform \
       --load \
       ${tags_cloud_run_chromium_flags[*]} \
@@ -250,6 +317,8 @@ if [ "$platform" = "linux/amd64" ]; then
   cmd="docker buildx build \
       --target gotenberg-cloudrun-libreoffice \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-cloudrun-libreoffice) \
       --platform $platform \
       --load \
       ${tags_cloud_run_libreoffice_flags[*]} \
@@ -263,6 +332,8 @@ if [ "$platform" = "linux/amd64" ] || [ "$platform" = "linux/arm64" ]; then
   cmd="docker buildx build \
       --target gotenberg-aws-lambda \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-aws-lambda) \
       --platform $platform \
       --load \
       ${tags_aws_lambda_flags[*]} \
@@ -273,6 +344,8 @@ if [ "$platform" = "linux/amd64" ] || [ "$platform" = "linux/arm64" ]; then
   cmd="docker buildx build \
       --target gotenberg-aws-lambda-chromium \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-aws-lambda-chromium) \
       --platform $platform \
       --load \
       ${tags_aws_lambda_chromium_flags[*]} \
@@ -283,6 +356,8 @@ if [ "$platform" = "linux/amd64" ] || [ "$platform" = "linux/arm64" ]; then
   cmd="docker buildx build \
       --target gotenberg-aws-lambda-libreoffice \
       --build-arg GOTENBERG_VERSION=$version \
+      --build-arg APT_SNAPSHOT=$apt_snapshot \
+      $(cache_flags gotenberg-aws-lambda-libreoffice) \
       --platform $platform \
       --load \
       ${tags_aws_lambda_libreoffice_flags[*]} \

.github/workflows/continuous-integration.yml

@@ -31,7 +31,7 @@ jobs:
       - name: Run linters
         uses: golangci/golangci-lint-action@v9
         with:
-          version: v2.12.2
+          version: v2.13.2
 
   lint-prettier:
     name: Lint non-Golang codebase

Makefile

@@ -33,11 +33,16 @@ API_OIDC_ISSUER=
 API_OIDC_AUDIENCE=
 API_OIDC_JWKS_URL=
 API_DOWNLOAD_FROM_ALLOW_LIST=
-API_DOWNLOAD_FROM_DENY_LIST=^https?://(10\.|172\.(1[6-9]|2[0-9]|3[01])\.|192\.168\.|169\.254\.|0\.0\.0\.0|127\.|localhost|\[::1\]|\[fd)
+# Empty, like the flag default since 8.32.0. A textual deny-list cannot
+# enumerate every way to write a private address, so *_DENY_PRIVATE_IPS is the
+# control to reach for. Left false here so local testing can reach the host.
+API_DOWNLOAD_FROM_DENY_LIST=
 API_DOWNLOAD_FROM_DENY_PRIVATE_IPS=false
 API_DOWNLOAD_FROM_DENY_PUBLIC_IPS=false
 API_DOWNLOAD_FROM_ENABLE_ENVIRONMENT_PROXY=false
 API_DOWNLOAD_FROM_MAX_RETRY=4
+API_DOWNLOAD_FROM_MAX_CONCURRENCY=10
+API_DOWNLOAD_FROM_MAX_ENTRIES=0
 API_DISABLE_DOWNLOAD_FROM=false
 API_DISABLE_HEALTH_CHECK_ROUTE_TELEMETRY=true
 API_DISABLE_ROOT_ROUTE_TELEMETRY=true
@@ -82,6 +87,7 @@ LOG_STD_FORMAT=auto
 LOG_STD_ENABLE_GCP_FIELDS=false
 LOG_STD_LEVEL_CASE=lower
 PDFENGINES_DISABLE_ROUTES=false
+PDFENGINES_MAX_CONCURRENCY=1
 PDFENGINES_MERGE_ENGINES=qpdf,pdfcpu,pdftk
 PDFENGINES_SPLIT_ENGINES=pdfcpu,qpdf,pdftk
 PDFENGINES_FLATTEN_ENGINES=qpdf
@@ -112,7 +118,8 @@ OTEL_EXPORTER_OTLP_ENDPOINT=http://otel-collector:4317
 OTEL_EXPORTER_OTLP_INSECURE=true
 WEBHOOK_ENABLE_SYNC_MODE=false
 WEBHOOK_ALLOW_LIST=
-WEBHOOK_DENY_LIST=^https?://(10\.|172\.(1[6-9]|2[0-9]|3[01])\.|192\.168\.|169\.254\.|0\.0\.0\.0|127\.|localhost|\[::1\]|\[fd)
+# See the note on API_DOWNLOAD_FROM_DENY_LIST.
+WEBHOOK_DENY_LIST=
 WEBHOOK_DENY_PRIVATE_IPS=false
 WEBHOOK_DENY_PUBLIC_IPS=false
 WEBHOOK_ENABLE_ENVIRONMENT_PROXY=false
@@ -210,11 +217,19 @@ lint-prettier: ## Lint non-Golang codebase
 
 .PHONY: lint-todo
 lint-todo: ## Find TODOs in Golang codebase
-	golangci-lint run --no-config --disable-all --enable godox
+	golangci-lint run --no-config --default=none --enable godox
 
+# TODO: restore a plain "go fix ./..." once the errorsastype modernizer stops
+# rewriting this codebase into code that does not compile. Re-check by dropping
+# the flag and running "make fmt && make lint". Removing the analyzer upstream
+# makes go fix fail with "flag provided but not defined", so this cannot rot
+# silently.
+#   errorsastype rewrites errors.As to errors.AsType[T] without checking that T
+#   satisfies error, which breaks on api.HttpError since it does not embed
+#   error. Still broken as of Go 1.27.1.
 .PHONY: fmt
 fmt: ## Format Golang codebase and "optimize" the dependencies
-	go fix ./...
+	go fix -errorsastype=false ./...
 	golangci-lint fmt
 	go mod tidy
 

build/Dockerfile

@@ -1,7 +1,7 @@
 # ARG instructions do not create additional layers. Instead, next layers will
 # concatenate them. Also, we have to repeat ARG instructions in each build
 # stage that uses them.
-ARG GOLANG_VERSION=1.26.5
+ARG GOLANG_VERSION=1.27.1
 
 # ----------------------------------------------
 # pdfcpu binary build stage
@@ -59,7 +59,14 @@ RUN go build -o gotenberg -ldflags "-s -w -X 'github.com/gotenberg/gotenberg/v8/
 # ----------------------------------------------
 FROM debian:13-slim AS custom-jre-stage
 
-RUN apt-get update -qq \
+# APT_SNAPSHOT busts every layer below it when CI rotates the value, weekly.
+# Without it a persistent build cache turns the unpinned "apt-get upgrade" into
+# a cache hit and the published image keeps shipping the package versions that
+# were current when the cache was first populated.
+ARG APT_SNAPSHOT=""
+
+RUN echo "apt snapshot: $APT_SNAPSHOT" \
+    && apt-get update -qq \
     && apt-get upgrade -yqq \
     && DEBIAN_FRONTEND=noninteractive apt-get install -y -qq --no-install-recommends default-jdk-headless binutils
 
@@ -88,7 +95,7 @@ RUN apt-get update -qq \
 
 WORKDIR /downloads
 
-RUN curl -Ls https://raw.githubusercontent.com/gotenberg/unoconverter/v0.4.0/unoconv -o unoconverter \
+RUN curl -Ls https://raw.githubusercontent.com/gotenberg/unoconverter/v0.5.0/unoconv -o unoconverter \
     && chmod +x unoconverter
 
 RUN curl -o pdftk-all.jar "https://gitlab.com/api/v4/projects/5024297/packages/generic/pdftk-java/$PDFTK_VERSION/pdftk-all.jar" \
@@ -114,9 +121,15 @@ FROM base-image-stage AS common-stage
 ARG GOTENBERG_USER_GID=1001
 ARG GOTENBERG_USER_UID=1001
 
+# See the note on APT_SNAPSHOT in custom-jre-stage. Declaring it here covers
+# every "apt-get upgrade" in the gotenberg, gotenberg-chromium and
+# gotenberg-libreoffice targets too, since all three branch from this stage.
+ARG APT_SNAPSHOT=""
+
 # Create a non-root user.
 # All processes in the Docker container will run with this dedicated user.
-RUN groupadd --gid "$GOTENBERG_USER_GID" gotenberg \
+RUN echo "apt snapshot: $APT_SNAPSHOT" \
+    && groupadd --gid "$GOTENBERG_USER_GID" gotenberg \
     && useradd --uid "$GOTENBERG_USER_UID" --gid gotenberg --shell /bin/bash --home /home/gotenberg --no-create-home gotenberg \
     && mkdir /home/gotenberg \
     && chown gotenberg: /home/gotenberg
@@ -259,7 +272,7 @@ RUN echo "deb http://deb.debian.org/debian trixie-backports main" >> /etc/apt/so
         hyphen-no hyphen-or hyphen-pa hyphen-pl hyphen-pt-br hyphen-pt-pt hyphen-ro hyphen-ru hyphen-sk hyphen-sl \
         hyphen-sr hyphen-sv hyphen-ta hyphen-te hyphen-th hyphen-uk hyphen-zu \
     && DEBIAN_FRONTEND=noninteractive apt-get install -y -qq --no-install-recommends -t trixie-backports \
-        libreoffice-writer libreoffice-calc libreoffice-impress libreoffice-draw python3-uno \
+        libreoffice-writer libreoffice-calc libreoffice-impress libreoffice-draw libreoffice-math python3-uno \
     # unoconverter will look for the Python binary, which has to be at version 3.
     && ln -s /usr/bin/python3 /usr/bin/python \
     # Cleanup.
@@ -386,7 +399,7 @@ RUN echo "deb http://deb.debian.org/debian trixie-backports main" >> /etc/apt/so
         hyphen-no hyphen-or hyphen-pa hyphen-pl hyphen-pt-br hyphen-pt-pt hyphen-ro hyphen-ru hyphen-sk hyphen-sl \
         hyphen-sr hyphen-sv hyphen-ta hyphen-te hyphen-th hyphen-uk hyphen-zu \
     && DEBIAN_FRONTEND=noninteractive apt-get install -y -qq --no-install-recommends -t trixie-backports \
-        libreoffice-writer libreoffice-calc libreoffice-impress libreoffice-draw python3-uno \
+        libreoffice-writer libreoffice-calc libreoffice-impress libreoffice-draw libreoffice-math python3-uno \
     # unoconverter will look for the Python binary, which has to be at version 3.
     && ln -s /usr/bin/python3 /usr/bin/python \
     # Cleanup.
@@ -485,7 +498,7 @@ FROM gotenberg AS gotenberg-aws-lambda
 
 USER root
 
-COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:0.9.1 /lambda-adapter /opt/extensions/lambda-adapter
+COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:1.0.1 /lambda-adapter /opt/extensions/lambda-adapter
 
 ENV AWS_LWA_PORT=3000
 ENV AWS_LWA_READINESS_CHECK_PATH=/health
@@ -503,7 +516,7 @@ FROM gotenberg-chromium AS gotenberg-aws-lambda-chromium
 
 USER root
 
-COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:0.9.1 /lambda-adapter /opt/extensions/lambda-adapter
+COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:1.0.1 /lambda-adapter /opt/extensions/lambda-adapter
 
 ENV AWS_LWA_PORT=3000
 ENV AWS_LWA_READINESS_CHECK_PATH=/health
@@ -521,7 +534,7 @@ FROM gotenberg-libreoffice AS gotenberg-aws-lambda-libreoffice
 
 USER root
 
-COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:0.9.1 /lambda-adapter /opt/extensions/lambda-adapter
+COPY --from=public.ecr.aws/awsguru/aws-lambda-adapter:1.0.1 /lambda-adapter /opt/extensions/lambda-adapter
 
 ENV AWS_LWA_PORT=3000
 ENV AWS_LWA_READINESS_CHECK_PATH=/health

cmd/gotenberg.go

@@ -80,7 +80,7 @@ func Run() {
 	// Override their values if the corresponding environment variables are
 	// set.
 	fs.VisitAll(func(f *flag.Flag) {
-		envName := strings.ToUpper(strings.ReplaceAll(f.Name, "-", "_"))
+		envName := gotenberg.EnvVarName(f.Name)
 		val, ok := os.LookupEnv(envName)
 		if !ok {
 			return

compose.yaml

@@ -35,6 +35,8 @@ services:
       - "--api-download-from-deny-public-ips=${API_DOWNLOAD_FROM_DENY_PUBLIC_IPS}"
       - "--api-download-from-enable-environment-proxy=${API_DOWNLOAD_FROM_ENABLE_ENVIRONMENT_PROXY}"
       - "--api-download-from-max-retry=${API_DOWNLOAD_FROM_MAX_RETRY}"
+      - "--api-download-from-max-concurrency=${API_DOWNLOAD_FROM_MAX_CONCURRENCY}"
+      - "--api-download-from-max-entries=${API_DOWNLOAD_FROM_MAX_ENTRIES}"
       - "--api-disable-download-from=${API_DISABLE_DOWNLOAD_FROM}"
       - "--api-disable-health-check-route-telemetry=${API_DISABLE_HEALTH_CHECK_ROUTE_TELEMETRY}"
       - "--api-disable-root-route-telemetry=${API_DISABLE_ROOT_ROUTE_TELEMETRY}"
@@ -94,6 +96,7 @@ services:
       - "--pdfengines-embed-engines=${PDFENGINES_EMBED_ENGINES}"
       - "--pdfengines-embed-metadata-engines=${PDFENGINES_EMBED_METADATA_ENGINES}"
       - "--pdfengines-factur-x-engines=${PDFENGINES_FACTUR_X_ENGINES}"
+      - "--pdfengines-max-concurrency=${PDFENGINES_MAX_CONCURRENCY}"
       - "--pdfengines-disable-routes=${PDFENGINES_DISABLE_ROUTES}"
       - "--prometheus-namespace=${PROMETHEUS_NAMESPACE}"
       - "--prometheus-collect-interval=${PROMETHEUS_COLLECT_INTERVAL}"

go.mod

@@ -1,53 +1,50 @@
 module github.com/gotenberg/gotenberg/v8
 
-go 1.26.5
+go 1.27.1
 
 require (
 	github.com/alexliesenfeld/health v0.8.1
 	github.com/chromedp/cdproto v0.0.0-20250803210736-d308e07a266d // pinned with chromedp v0.14.2, see below
 	github.com/chromedp/chromedp v0.14.2 // pinned: v0.15.x breaks the headless print-mode paint pipeline (rAF / ResizeObserver / IntersectionObserver stop firing, blank charts). See https://github.com/gotenberg/gotenberg/issues/1535.
+	github.com/coreos/go-oidc/v3 v3.21.0
 	github.com/cucumber/godog v0.16.0
-	github.com/dlclark/regexp2 v1.12.0
-	github.com/gomarkdown/markdown v0.0.0-20260725000948-8435af3f5984
+	github.com/dlclark/regexp2/v2 v2.8.0
+	github.com/gomarkdown/markdown v0.0.0-20260824154242-13c5cf49db8d
 	github.com/google/uuid v1.6.0
 	github.com/hashicorp/go-retryablehttp v0.7.8
-	github.com/labstack/echo/v4 v4.15.4
+	github.com/labstack/echo/v5 v5.3.1
 	github.com/labstack/gommon v0.5.0
 	github.com/mholt/archives v0.1.5
 	github.com/microcosm-cc/bluemonday v1.0.27
-	github.com/moby/moby/api v1.55.0
-	github.com/moby/moby/client v0.5.1
+	github.com/moby/moby/api v1.56.0
+	github.com/moby/moby/client v0.6.0
 	github.com/prometheus/client_golang v1.24.1
-	github.com/shirou/gopsutil/v4 v4.26.7
+	github.com/shirou/gopsutil/v4 v4.26.8
 	github.com/spf13/pflag v1.0.10
-	github.com/stretchr/testify v1.11.1
+	github.com/stretchr/testify v1.12.1
 	github.com/testcontainers/testcontainers-go v0.44.0
-	go.opentelemetry.io/contrib/bridges/otelslog v0.20.0
-	go.opentelemetry.io/contrib/exporters/autoexport v0.70.0
-	go.opentelemetry.io/otel v1.45.0
-	go.opentelemetry.io/otel/log v0.21.0
-	go.opentelemetry.io/otel/metric v1.45.0
-	go.opentelemetry.io/otel/sdk v1.45.0
-	go.opentelemetry.io/otel/sdk/log v0.21.0
-	go.opentelemetry.io/otel/sdk/metric v1.45.0
-	go.opentelemetry.io/otel/trace v1.45.0
+	go.opentelemetry.io/contrib/bridges/otelslog v0.20.1
+	go.opentelemetry.io/contrib/exporters/autoexport v0.71.0
+	go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp v0.71.0
+	go.opentelemetry.io/otel v1.46.0
+	go.opentelemetry.io/otel/log v0.22.0
+	go.opentelemetry.io/otel/metric v1.46.0
+	go.opentelemetry.io/otel/sdk v1.46.0
+	go.opentelemetry.io/otel/sdk/log v0.22.0
+	go.opentelemetry.io/otel/sdk/metric v1.46.0
+	go.opentelemetry.io/otel/trace v1.46.0
 	golang.org/x/net v0.58.0
-	golang.org/x/sync v0.22.0
+	golang.org/x/sync v0.23.0
 	golang.org/x/term v0.45.0
 	golang.org/x/text v0.41.0
 )
 
-require (
-	github.com/coreos/go-oidc/v3 v3.20.0
-	go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp v0.70.0
-)
-
 require (
 	dario.cat/mergo v1.0.2 // indirect
 	github.com/Azure/go-ansiterm v0.0.0-20250102033503-faa5f7b0171c // indirect
 	github.com/Microsoft/go-winio v0.6.2 // indirect
 	github.com/STARRY-S/zip v0.2.3 // indirect
-	github.com/andybalholm/brotli v1.2.2 // indirect
+	github.com/andybalholm/brotli v1.2.3 // indirect
 	github.com/aymerick/douceur v0.2.0 // indirect
 	github.com/beorn7/perks v1.0.1 // indirect
 	github.com/bodgit/plumbing v1.3.0 // indirect
@@ -64,15 +61,14 @@ require (
 	github.com/cpuguy83/dockercfg v0.3.2 // indirect
 	github.com/cucumber/gherkin/go/v42 v42.0.1 // indirect
 	github.com/cucumber/messages/go/v34 v34.2.1 // indirect
-	github.com/davecgh/go-spew v1.1.1 // indirect
 	github.com/distribution/reference v0.6.0 // indirect
 	github.com/docker/go-connections v0.8.1 // indirect
 	github.com/docker/go-units v0.5.0 // indirect
 	github.com/dsnet/compress v0.0.2-0.20230904184137-39efe44ab707 // indirect
-	github.com/ebitengine/purego v0.10.2 // indirect
+	github.com/ebitengine/purego v0.11.0 // indirect
 	github.com/felixge/httpsnoop v1.1.0 // indirect
-	github.com/go-jose/go-jose/v4 v4.1.4 // indirect
-	github.com/go-json-experiment/json v0.0.0-20260623181947-01eb4420fa68 // indirect
+	github.com/go-jose/go-jose/v4 v4.1.5 // indirect
+	github.com/go-json-experiment/json v0.0.0-20260820222146-c27c302e5fc3 // indirect
 	github.com/go-logr/logr v1.4.4 // indirect
 	github.com/go-logr/stdr v1.2.2 // indirect
 	github.com/go-ole/go-ole v1.3.0 // indirect
@@ -86,7 +82,7 @@ require (
 	github.com/hashicorp/go-memdb v1.3.5 // indirect
 	github.com/hashicorp/golang-lru v1.0.2 // indirect
 	github.com/hashicorp/golang-lru/v2 v2.0.7 // indirect
-	github.com/klauspost/compress v1.19.2 // indirect
+	github.com/klauspost/compress v1.20.0 // indirect
 	github.com/klauspost/pgzip v1.2.6 // indirect
 	github.com/lufia/plan9stats v0.0.0-20260802145828-341c2f0c90b5 // indirect
 	github.com/magiconair/properties v1.18.11 // indirect
@@ -102,48 +98,45 @@ require (
 	github.com/moby/sys/userns v0.2.0 // indirect
 	github.com/moby/term v0.5.2 // indirect
 	github.com/munnerz/goautoneg v0.0.0-20191010083416-a7dc8b61c822 // indirect
-	github.com/nwaples/rardecode/v2 v2.3.0 // indirect
+	github.com/nwaples/rardecode/v2 v2.4.1 // indirect
 	github.com/opencontainers/go-digest v1.0.0 // indirect
 	github.com/opencontainers/image-spec v1.1.1 // indirect
-	github.com/pierrec/lz4/v4 v4.1.28 // indirect
-	github.com/pmezard/go-difflib v1.0.0 // indirect
+	github.com/pierrec/lz4/v4 v4.1.29 // indirect
 	github.com/power-devops/perfstat v0.0.0-20260805114148-88456608a4f6 // indirect
-	github.com/prometheus/client_model v0.6.2 // indirect
-	github.com/prometheus/common v0.70.1 // indirect
+	github.com/prometheus/client_model v0.6.3 // indirect
+	github.com/prometheus/common v0.71.0 // indirect
 	github.com/prometheus/otlptranslator v1.0.0 // indirect
-	github.com/prometheus/procfs v0.21.1 // indirect
-	github.com/sirupsen/logrus v1.10.0 // indirect
+	github.com/prometheus/procfs v0.22.0 // indirect
+	github.com/sirupsen/logrus v1.10.2 // indirect
 	github.com/sorairolake/lzip-go v0.3.8 // indirect
 	github.com/spf13/afero v1.15.0 // indirect
 	github.com/stangelandcl/ppmd v0.1.1 // indirect
 	github.com/tklauser/go-sysconf v0.4.0 // indirect
 	github.com/tklauser/numcpus v0.12.0 // indirect
 	github.com/ulikunitz/xz v0.5.16 // indirect
-	github.com/valyala/bytebufferpool v1.0.0 // indirect
-	github.com/valyala/fasttemplate v1.2.2 // indirect
 	github.com/yusufpapurcu/wmi v1.2.4 // indirect
 	go.opentelemetry.io/auto/sdk v1.2.1 // indirect
-	go.opentelemetry.io/contrib/bridges/prometheus v0.70.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlplog/otlploggrpc v0.21.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlplog/otlploghttp v0.21.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlpmetric/otlpmetricgrpc v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlpmetric/otlpmetrichttp v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlptrace v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracegrpc v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracehttp v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/prometheus v0.67.0 // indirect
-	go.opentelemetry.io/otel/exporters/stdout/stdoutlog v0.21.0 // indirect
-	go.opentelemetry.io/otel/exporters/stdout/stdoutmetric v1.45.0 // indirect
-	go.opentelemetry.io/otel/exporters/stdout/stdouttrace v1.45.0 // indirect
+	go.opentelemetry.io/contrib/bridges/prometheus v0.71.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlplog/otlploggrpc v0.22.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlplog/otlploghttp v0.22.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlpmetric/otlpmetricgrpc v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlpmetric/otlpmetrichttp v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlptrace v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracegrpc v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracehttp v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/prometheus v0.68.0 // indirect
+	go.opentelemetry.io/otel/exporters/stdout/stdoutlog v0.22.0 // indirect
+	go.opentelemetry.io/otel/exporters/stdout/stdoutmetric v1.46.0 // indirect
+	go.opentelemetry.io/otel/exporters/stdout/stdouttrace v1.46.0 // indirect
 	go.opentelemetry.io/proto/otlp v1.11.0 // indirect
+	go.yaml.in/yaml/v3 v3.0.5 // indirect
 	go4.org v0.0.0-20260112195520-a5071408f32f // indirect
-	golang.org/x/crypto v0.55.0 // indirect
+	golang.org/x/crypto v0.56.0 // indirect
 	golang.org/x/oauth2 v0.36.0 // indirect
 	golang.org/x/sys v0.47.0 // indirect
 	golang.org/x/time v0.15.0 // indirect
-	google.golang.org/genproto/googleapis/api v0.0.0-20260810153831-ec0a7760b754 // indirect
-	google.golang.org/genproto/googleapis/rpc v0.0.0-20260810153831-ec0a7760b754 // indirect
-	google.golang.org/grpc v1.83.0 // indirect
+	google.golang.org/genproto/googleapis/api v0.0.0-20260831171406-18b4a7587f8a // indirect
+	google.golang.org/genproto/googleapis/rpc v0.0.0-20260831171406-18b4a7587f8a // indirect
+	google.golang.org/grpc v1.83.2 // indirect
 	google.golang.org/protobuf v1.36.12 // indirect
-	gopkg.in/yaml.v3 v3.0.1 // indirect
 )

go.sum

@@ -10,8 +10,8 @@ github.com/STARRY-S/zip v0.2.3 h1:luE4dMvRPDOWQdeDdUxUoZkzUIpTccdKdhHHsQJ1fm4=
 github.com/STARRY-S/zip v0.2.3/go.mod h1:lqJ9JdeRipyOQJrYSOtpNAiaesFO6zVDsE8GIGFaoSk=
 github.com/alexliesenfeld/health v0.8.1 h1:wdE3vt+cbJotiR8DGDBZPKHDFoJbAoWEfQTcqrmedUg=
 github.com/alexliesenfeld/health v0.8.1/go.mod h1:TfNP0f+9WQVWMQRzvMUjlws4ceXKEL3WR+6Hp95HUFc=
-github.com/andybalholm/brotli v1.2.2 h1:HzTuoo2ErYQqf5qvcJInB8uvqSVxRttzkFexPWtnceM=
-github.com/andybalholm/brotli v1.2.2/go.mod h1:rzTDkvFWvIrjDXZHkuS16NPggd91W3kUSvPlQ1pLaKY=
+github.com/andybalholm/brotli v1.2.3 h1:8H1qwOkl2LPfjf3YezB90JnCliZb6SInJ/OJkEbA5NQ=
+github.com/andybalholm/brotli v1.2.3/go.mod h1:rzTDkvFWvIrjDXZHkuS16NPggd91W3kUSvPlQ1pLaKY=
 github.com/aymerick/douceur v0.2.0 h1:Mv+mAeH1Q+n9Fr+oyamOlAkUNPWPlA8PPGR0QAaYuPk=
 github.com/aymerick/douceur v0.2.0/go.mod h1:wlT5vV2O3h55X9m7iVYN0TBM0NH/MmbLnd30/FjWUq4=
 github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
@@ -42,8 +42,8 @@ github.com/containerd/log v0.1.0 h1:TCJt7ioM2cr/tfR8GPbGf9/VRAX8D2B4PjzCpfX540I=
 github.com/containerd/log v0.1.0/go.mod h1:VRRf09a7mHDIRezVKTRCrOq78v577GXq3bSa3EhrzVo=
 github.com/containerd/platforms v0.2.1 h1:zvwtM3rz2YHPQsF2CHYM8+KtB5dvhISiXh5ZpSBQv6A=
 github.com/containerd/platforms v0.2.1/go.mod h1:XHCb+2/hzowdiut9rkudds9bE5yJ7npe7dG/wG+uFPw=
-github.com/coreos/go-oidc/v3 v3.20.0 h1:EtE0WIBHk03N+DqGkY4+UONzzZHk7amKt6IyNd7OsZE=
-github.com/coreos/go-oidc/v3 v3.20.0/go.mod h1:DYCf24+ncYi+XkIH97GY1+dqoRlbaSI26KVTCI9SrY4=
+github.com/coreos/go-oidc/v3 v3.21.0 h1:wZo4Q9Pum8dYEj0eMUPrqR+kvuGkeUplbLpNCkBqoWM=
+github.com/coreos/go-oidc/v3 v3.21.0/go.mod h1:DYCf24+ncYi+XkIH97GY1+dqoRlbaSI26KVTCI9SrY4=
 github.com/cpuguy83/dockercfg v0.3.2 h1:DlJTyZGBDlXqUZ2Dk2Q3xHs/FtnooJJVaad2S9GKorA=
 github.com/cpuguy83/dockercfg v0.3.2/go.mod h1:sugsbF4//dDlL/i+S+rtpIWp+5h0BHJHfjj5/jFyUJc=
 github.com/creack/pty v1.1.24 h1:bJrF4RRfyJnbTJqzRLHzcGaZK1NeM5kTC9jGgovnR1s=
@@ -55,12 +55,11 @@ github.com/cucumber/godog v0.16.0/go.mod h1:EDUX9yCqANK+GpbftMDeu61sUDtdLuo1JJgX
 github.com/cucumber/messages/go/v34 v34.2.1 h1:qBPEl+HhNJuRX8Kjaw1Pm60KOODZf2/4WQAi0SR/neE=
 github.com/cucumber/messages/go/v34 v34.2.1/go.mod h1:LYUPjqlTS1kS0pdkdf6sS5uirnjwiIzEGyXPezXNhL8=
 github.com/davecgh/go-spew v1.1.0/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
-github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c=
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/distribution/reference v0.6.0 h1:0IXCQ5g4/QMHHkarYzh5l+u8T3t73zM5QvfrDyIgxBk=
 github.com/distribution/reference v0.6.0/go.mod h1:BbU0aIcezP1/5jX/8MP0YiH4SdvB5Y4f/wlDRiLyi3E=
-github.com/dlclark/regexp2 v1.12.0 h1:0j4c5qQmnC6XOWNjP3PIXURXN2gWx76rd3KvgdPkCz8=
-github.com/dlclark/regexp2 v1.12.0/go.mod h1:DHkYz0B9wPfa6wondMfaivmHpzrQ3v9q8cnmRbL6yW8=
+github.com/dlclark/regexp2/v2 v2.8.0 h1:CekDhPLGfm+GAJmPVFIG+5dqMIQPkyHJll7BbdneDfw=
+github.com/dlclark/regexp2/v2 v2.8.0/go.mod h1:avUrQvPaLz2DrFNHJF0taWAFFX2C1GMSSoeiqFjcBmU=
 github.com/docker/go-connections v0.8.1 h1:JibmG5hULs5qXSr/cp/w3Pw5fZuStt4MOHMUExb29/M=
 github.com/docker/go-connections v0.8.1/go.mod h1:no1qkHdjq7kLMGUXYAduOhYPSJxxvgWBh7ogVvptn3Q=
 github.com/docker/go-units v0.5.0 h1:69rxXcBk27SvSaaxTtLh/8llcHD8vYHT7WSdRZ/jvr4=
@@ -68,16 +67,16 @@ github.com/docker/go-units v0.5.0/go.mod h1:fgPhTUdO+D/Jk86RDLlptpiXQzgHJF7gydDD
 github.com/dsnet/compress v0.0.2-0.20230904184137-39efe44ab707 h1:2tV76y6Q9BB+NEBasnqvs7e49aEBFI8ejC89PSnWH+4=
 github.com/dsnet/compress v0.0.2-0.20230904184137-39efe44ab707/go.mod h1:qssHWj60/X5sZFNxpG4HBPDHVqxNm4DfnCKgrbZOT+s=
 github.com/dsnet/golib v0.0.0-20171103203638-1ea166775780/go.mod h1:Lj+Z9rebOhdfkVLjJ8T6VcRQv3SXugXy999NBtR9aFY=
-github.com/ebitengine/purego v0.10.2 h1:W809HbnvzAxgdm+aOvlSekrM16wGCdT/e76+9tS7gzE=
-github.com/ebitengine/purego v0.10.2/go.mod h1:iIjxzd6CiRiOG0UyXP+V1+jWqUXVjPKLAI0mRfJZTmQ=
+github.com/ebitengine/purego v0.11.0 h1:jhp/D+Nyv7UUW8HAcmcjt2N2rYrYi9m3SL21k0Ua/NI=
+github.com/ebitengine/purego v0.11.0/go.mod h1:DCHPP08djqhNSoTfImcnHYQRZmd0qhakvrozqaEYhGQ=
 github.com/fatih/color v1.16.0 h1:zmkK9Ngbjj+K0yRhTVONQh1p/HknKYSlNT+vZCzyokM=
 github.com/fatih/color v1.16.0/go.mod h1:fL2Sau1YI5c0pdGEVCbKQbLXB6edEj1ZgiY4NijnWvE=
 github.com/felixge/httpsnoop v1.1.0 h1:3YtUj32ZZkqZtt3sZZsClsymw/QDuVfpNhoA31zeORc=
 github.com/felixge/httpsnoop v1.1.0/go.mod h1:Zqxgdd+1Rkcz8euOqdr7lqgCRJztwr5hp9vDSi5UZCE=
-github.com/go-jose/go-jose/v4 v4.1.4 h1:moDMcTHmvE6Groj34emNPLs/qtYXRVcd6S7NHbHz3kA=
-github.com/go-jose/go-jose/v4 v4.1.4/go.mod h1:x4oUasVrzR7071A4TnHLGSPpNOm2a21K9Kf04k1rs08=
-github.com/go-json-experiment/json v0.0.0-20260623181947-01eb4420fa68 h1:KZaTBSyshWX3MP5jukJcNSuXDQTO+rNpt0J564dX/eg=
-github.com/go-json-experiment/json v0.0.0-20260623181947-01eb4420fa68/go.mod h1:tphK2c80bpPhMOI4v6bIc2xWywPfbqi1Z06+RcrMkDg=
+github.com/go-jose/go-jose/v4 v4.1.5 h1:RjgjO2LOtWOJKUC5wpwY9LR3B3vwVAz6JS2YHfYU6eA=
+github.com/go-jose/go-jose/v4 v4.1.5/go.mod h1:x4oUasVrzR7071A4TnHLGSPpNOm2a21K9Kf04k1rs08=
+github.com/go-json-experiment/json v0.0.0-20260820222146-c27c302e5fc3 h1:UADEEmDKgfXbtnGJZ97beY5XLo9ZechG1nlU4KnRrkE=
+github.com/go-json-experiment/json v0.0.0-20260820222146-c27c302e5fc3/go.mod h1:tphK2c80bpPhMOI4v6bIc2xWywPfbqi1Z06+RcrMkDg=
 github.com/go-logr/logr v1.2.2/go.mod h1:jdQByPbusPIv2/zmleS9BjJVeZ6kBagPoEUsqbVz/1A=
 github.com/go-logr/logr v1.4.4 h1:tG4xh9yMsRCAiodLVTxyrkzSZ9+o0L1Kg/+cPVcbP/8=
 github.com/go-logr/logr v1.4.4/go.mod h1:9T104GzyrTigFIr8wt5mBrctHMim0Nb2HLGrmQ40KvY=
@@ -94,8 +93,8 @@ github.com/gobwas/ws v1.4.0 h1:CTaoG1tojrh4ucGPcoJFiAQUAsEWekEWvLy7GsVNqGs=
 github.com/gobwas/ws v1.4.0/go.mod h1:G3gNqMNtPppf5XUz7O4shetPpcZ1VJ7zt18dlUeakrc=
 github.com/golang/protobuf v1.5.4 h1:i7eJL8qZTpSEXOPTxNKhASYpMn+8e5Q6AdndVa1dWek=
 github.com/golang/protobuf v1.5.4/go.mod h1:lnTiLA8Wa4RWRcIUkrtSVa5nRhsEGBg48fD6rSs7xps=
-github.com/gomarkdown/markdown v0.0.0-20260725000948-8435af3f5984 h1:6DE2PprLLZelQJu7AeebZLxjcENwC1plRZHDvd5uMCU=
-github.com/gomarkdown/markdown v0.0.0-20260725000948-8435af3f5984/go.mod h1:JDGcbDT52eL4fju3sZ4TeHGsQwhG9nbDV21aMyhwPoA=
+github.com/gomarkdown/markdown v0.0.0-20260824154242-13c5cf49db8d h1:8VtgBGEPLZ2Yn0Fuh6Pwmy3qF6indeaqy8mrBMbUKRQ=
+github.com/gomarkdown/markdown v0.0.0-20260824154242-13c5cf49db8d/go.mod h1:JDGcbDT52eL4fju3sZ4TeHGsQwhG9nbDV21aMyhwPoA=
 github.com/google/go-cmp v0.5.5/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
 github.com/google/go-cmp v0.7.0 h1:wk8382ETsv4JYUZwIsn6YpYiWiBsYLSJiTsyBybVuN8=
 github.com/google/go-cmp v0.7.0/go.mod h1:pXiqmnSA92OHEEa9HXL2W4E7lf9JzCmGVUdgjX3N/iU=
@@ -125,19 +124,15 @@ github.com/hashicorp/golang-lru v1.0.2/go.mod h1:iADmTwqILo4mZ8BN3D2Q6+9jd8WM5uG
 github.com/hashicorp/golang-lru/v2 v2.0.7 h1:a+bsQ5rvGLjzHuww6tVxozPZFVghXaHOwFs4luLUK2k=
 github.com/hashicorp/golang-lru/v2 v2.0.7/go.mod h1:QeFd9opnmA6QUJc5vARoKUSoFhyfM2/ZepoAG6RGpeM=
 github.com/klauspost/compress v1.4.1/go.mod h1:RyIbtBH6LamlWaDj8nUwkbUhJ87Yi3uG0guNDohfE1A=
-github.com/klauspost/compress v1.19.2 h1:hMRETovs/pu/dVWN7zIT1PGG8t509MwT6bO7XSi26R8=
-github.com/klauspost/compress v1.19.2/go.mod h1:cwPg85FWrGar70rWktvGQj8/hthj3wpl0PGDogxkrSQ=
+github.com/klauspost/compress v1.20.0 h1:a3C1ke2ohxFymNlb2HWAHjDeKCI90scRskErZkR0ezA=
+github.com/klauspost/compress v1.20.0/go.mod h1:LUdAzn7YLVvxLpc7y3V1m40wESHTgc1422pwwBSKYuI=
 github.com/klauspost/cpuid v1.2.0/go.mod h1:Pj4uuM528wm8OyEC2QMXAi2YiTZ96dNQPGgoMS4s3ek=
 github.com/klauspost/pgzip v1.2.6 h1:8RXeL5crjEUFnR2/Sn6GJNWtSQ3Dk8pq4CL3jvdDyjU=
 github.com/klauspost/pgzip v1.2.6/go.mod h1:Ch1tH69qFZu15pkjo5kYi6mth2Zzwzt50oCQKQE9RUs=
-github.com/kr/pretty v0.3.1 h1:flRD4NNwYAUpkphVc1HcthR4KEIFJ65n8Mw5qdRn3LE=
-github.com/kr/pretty v0.3.1/go.mod h1:hoEshYVHaxMs3cyo3Yncou5ZscifuDolrwPKZanG3xk=
-github.com/kr/text v0.2.0 h1:5Nx0Ya0ZqY2ygV366QzturHI13Jq95ApcVaJBhpS+AY=
-github.com/kr/text v0.2.0/go.mod h1:eLer722TekiGuMkidMxC/pM04lWEeraHUUmBw8l2grE=
 github.com/kylelemons/godebug v1.1.0 h1:RPNrshWIDI6G2gRW9EHilWtl7Z6Sb1BR0xunSBf0SNc=
 github.com/kylelemons/godebug v1.1.0/go.mod h1:9/0rRGxNHcop5bhtWyNeEfOS8JIWk580+fNqagV/RAw=
-github.com/labstack/echo/v4 v4.15.4 h1:DL45vVYa+BWE+XuW+zZNd9H0YEdZ80UAWJGcTVW4EVs=
-github.com/labstack/echo/v4 v4.15.4/go.mod h1:CuMetKIRwsuO/qlAgMq+KTAalwGoB/h4tC+yPdrTj1g=
+github.com/labstack/echo/v5 v5.3.1 h1:75maCxkQVGualckLc/5s/ihgpH1a1Dc6AuGWNVNs6bw=
+github.com/labstack/echo/v5 v5.3.1/go.mod h1:4iEGNQiPPZnkfYpNR/L6fINd3NLiGWUD5+eBotFALas=
 github.com/labstack/gommon v0.5.0 h1:6VSQ2NOzsnEJ5W6+84E0RbcaDDmgB6NIAzWCczTEe6c=
 github.com/labstack/gommon v0.5.0/go.mod h1:Rzlg7HHy1maLfzBYGg9NZcVuz1sA68HHhLjhcEllYE0=
 github.com/ledongthuc/pdf v0.0.0-20220302134840-0c2507a12d80 h1:6Yzfa6GP0rIo/kULo2bwGEkFvCePZ3qHDDTC3/J9Swo=
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@@ -228,8 +220,8 @@ github.com/stretchr/objx v0.5.3/go.mod h1:rDQraq+vQZU7Fde9LOZLr8Tax6zZvy4kuNKF+Q
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@@ -239,80 +231,78 @@ github.com/tklauser/numcpus v0.12.0/go.mod h1:ABHeXzJnr/qqwguhClkZKT1/8VABcYrsyU
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 go.uber.org/goleak v1.3.0 h1:2K3zAYmnTNqV73imy9J1T3WC+gmCePx2hEGkimedGto=
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 go.yaml.in/yaml/v2 v2.4.4 h1:tuyd0P+2Ont/d6e2rl3be67goVK4R6deVxCUX5vyPaQ=
 go.yaml.in/yaml/v2 v2.4.4/go.mod h1:gMZqIpDtDqOfM0uNfy0SkpRhvUryYH0Z6wdMYcacYXQ=
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 go4.org v0.0.0-20260112195520-a5071408f32f h1:ziUVAjmTPwQMBmYR1tbdRFJPtTcQUI12fH9QQjfb0Sw=
 go4.org v0.0.0-20260112195520-a5071408f32f/go.mod h1:ZRJnO5ZI4zAwMFp+dS1+V6J6MSyAowhRqAE+DPa1Xp0=
-golang.org/x/crypto v0.55.0 h1:+KWHjbgOaAQ66dh/YlkZKHlz9ZUlq61AFirAR9ntP8M=
-golang.org/x/crypto v0.55.0/go.mod h1:uq0V9dE/fzQuJtbnL+2EhWOE63vo164FY8xqEnV9xis=
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-golang.org/x/sync v0.22.0 h1:SZjpbeLmrCk4xhRSZFNZW5gFUeCeFgjekvI/+gfScek=
-golang.org/x/sync v0.22.0/go.mod h1:9xrNwdLfx4jkKbNva9FpL6vEN7evnE43NNNJQ2LF3+0=
+golang.org/x/sync v0.23.0 h1:KameEIfc1IkluZyXWLn39Wd4tURc6GbCiISGiZm2bQk=
+golang.org/x/sync v0.23.0/go.mod h1:sUUOizhqBxiL6pEWpqNLUiaJn1ShEbZ6BBqskPbjZm0=
 golang.org/x/sys v0.0.0-20190916202348-b4ddaad3f8a3/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
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@@ -329,19 +319,16 @@ golang.org/x/time v0.15.0/go.mod h1:Y4YMaQmXwGQZoFaVFk4YpCt4FLQMYKZe9oeV/f4MSno=
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-google.golang.org/genproto/googleapis/api v0.0.0-20260810153831-ec0a7760b754 h1:dWeMvEJ3JhYgqSCAHUZZJgMUyfniiiCvDc72x5EqJP0=
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pkg/gotenberg/allowlist.go

@@ -0,0 +1,635 @@
+package gotenberg
+
+import (
+	"strings"
+)
+
+// AllowListRisk classifies why an allow-list pattern is dangerous. A URL that
+// matches an allow-list skips the private and public IP checks, so a pattern
+// that matches more than its author intended silently widens outbound access.
+// See [AuditAllowList].
+type AllowListRisk string
+
+const (
+	// AllowListRiskUnanchored marks a pattern with no leading "^". regexp2
+	// searches rather than matches, so the pattern hits anywhere in the URL,
+	// including the query string.
+	AllowListRiskUnanchored AllowListRisk = "unanchored"
+
+	// AllowListRiskUnanchoredBranch marks an alternation whose later branches
+	// have no leading "^". Anchoring only the first branch is a common slip.
+	AllowListRiskUnanchoredBranch AllowListRisk = "unanchored-branch"
+
+	// AllowListRiskCatchAll marks a pattern with no literal prefix, such as
+	// ".+", which matches every URL and disables filtering entirely.
+	AllowListRiskCatchAll AllowListRisk = "catch-all"
+
+	// AllowListRiskOpenHost marks a pattern whose host is not terminated, so
+	// it also matches attacker-chosen suffix hosts. For example
+	// "^https://trusted\.example\.com" matches
+	// "https://trusted.example.com.attacker.example/".
+	AllowListRiskOpenHost AllowListRisk = "open-host"
+)
+
+// AllowListFinding reports one risky entry of an allow-list.
+type AllowListFinding struct {
+	// Index is the zero-based position of the pattern within the flag value.
+	Index int
+
+	// Pattern is the operator's pattern, verbatim.
+	Pattern string
+
+	// Risk is why the pattern is dangerous.
+	Risk AllowListRisk
+}
+
+// maxAuditedPatternLength bounds the patterns [AuditAllowList] inspects. A
+// pathological pattern is not worth walking, and reporting nothing is better
+// than reporting a partial verdict.
+const maxAuditedPatternLength = 4096
+
+// AuditAllowList reports the entries of an allow-list that match more URLs
+// than their author is likely to intend. It is a lint over the pattern source,
+// not a parser: it recognizes the shapes that are dangerous in practice and
+// stays silent when it cannot be sure.
+//
+// Callers use the findings to warn operators. Never use them to reject a
+// configuration: existing deployments rely on loose patterns, and a pattern
+// this function does not flag is not thereby safe.
+func AuditAllowList(patterns []string) []AllowListFinding {
+	var findings []AllowListFinding
+
+	for i, pattern := range patterns {
+		if pattern == "" || len(pattern) > maxAuditedPatternLength {
+			continue
+		}
+
+		risk, ok := auditPattern(pattern)
+		if ok {
+			findings = append(findings, AllowListFinding{Index: i, Pattern: pattern, Risk: risk})
+		}
+	}
+
+	return findings
+}
+
+// auditPattern classifies a single pattern, reporting the first risk found.
+func auditPattern(pattern string) (AllowListRisk, bool) {
+	body := trimInlineFlags(pattern)
+
+	branches := splitTopLevelAlternation(body)
+	for i, branch := range branches {
+		branch = strings.TrimSpace(branch)
+
+		anchored := hasStartAnchor(branch)
+		rest := strings.TrimPrefix(strings.TrimPrefix(branch, `\A`), "^")
+
+		// Catch-all first: a pattern that constrains nothing matches every URL
+		// whether or not it is anchored, and saying so is more useful than
+		// telling the operator to anchor it.
+		if literalPrefix(rest) == "" {
+			return AllowListRiskCatchAll, true
+		}
+
+		if !anchored {
+			if i == 0 {
+				return AllowListRiskUnanchored, true
+			}
+			return AllowListRiskUnanchoredBranch, true
+		}
+
+		// A lookaround invalidates the token walk, so skip the host check for
+		// this branch rather than guess. The anchor and catch-all checks above
+		// still applied.
+		if containsLookaround(rest) {
+			continue
+		}
+
+		if hostIsOpen(rest) {
+			return AllowListRiskOpenHost, true
+		}
+	}
+
+	return "", false
+}
+
+// trimInlineFlags removes a leading inline flag group such as "(?i)" so that
+// the anchor check sees the pattern proper.
+func trimInlineFlags(pattern string) string {
+	if !strings.HasPrefix(pattern, "(?") {
+		return pattern
+	}
+
+	end := strings.Index(pattern, ")")
+	if end == -1 {
+		return pattern
+	}
+
+	// Only a flag group qualifies. "(?:", "(?=", "(?!" and "(?<" open a real
+	// group and must stay.
+	flags := pattern[2:end]
+	if flags == "" || strings.ContainsAny(flags, ":=!<") {
+		return pattern
+	}
+	for _, r := range flags {
+		if !strings.ContainsRune("imsUx-", r) {
+			return pattern
+		}
+	}
+
+	return pattern[end+1:]
+}
+
+// hasStartAnchor reports whether branch begins with a start-of-input anchor.
+func hasStartAnchor(branch string) bool {
+	return strings.HasPrefix(branch, "^") || strings.HasPrefix(branch, `\A`)
+}
+
+// containsLookaround reports whether the pattern uses a lookaround, which the
+// token walk in [hostIsOpen] cannot reason about.
+func containsLookaround(s string) bool {
+	return strings.Contains(s, "(?=") || strings.Contains(s, "(?!") || strings.Contains(s, "(?<")
+}
+
+// splitTopLevelAlternation splits on "|" at paren depth zero, honoring escapes
+// and character classes.
+func splitTopLevelAlternation(s string) []string {
+	var (
+		parts   []string
+		current strings.Builder
+		depth   int
+		inClass bool
+	)
+
+	for i := 0; i < len(s); i++ {
+		c := s[i]
+
+		switch {
+		case c == '\\' && i+1 < len(s):
+			current.WriteByte(c)
+			current.WriteByte(s[i+1])
+			i++
+			continue
+		case c == '[' && !inClass:
+			inClass = true
+		case c == ']' && inClass:
+			inClass = false
+		case c == '(' && !inClass:
+			depth++
+		case c == ')' && !inClass:
+			depth--
+		case c == '|' && !inClass && depth == 0:
+			parts = append(parts, current.String())
+			current.Reset()
+			continue
+		}
+
+		current.WriteByte(c)
+	}
+
+	parts = append(parts, current.String())
+
+	return parts
+}
+
+// literalPrefix returns the characters a matching URL must start with. It
+// stops at the first optional or non-literal token, and descends one level
+// into a leading mandatory group so that "^(https|http)://" is not mistaken
+// for a catch-all. An empty result means the pattern constrains nothing.
+func literalPrefix(s string) string {
+	var prefix strings.Builder
+
+	for i := 0; i < len(s); {
+		// A group: descend once when it is mandatory, otherwise stop.
+		if s[i] == '(' {
+			end := matchingParen(s, i)
+			if end == -1 {
+				break
+			}
+			if isQuantified(s, end+1) {
+				break
+			}
+
+			inner := trimInlineFlags(s[i+1 : end])
+			branches := splitTopLevelAlternation(inner)
+
+			common := literalPrefix(branches[0])
+			for _, b := range branches[1:] {
+				common = commonPrefix(common, literalPrefix(b))
+			}
+			prefix.WriteString(common)
+
+			// Only the leading group is worth descending into.
+			break
+		}
+
+		var token string
+		switch {
+		case s[i] == '\\' && i+1 < len(s):
+			token = s[i : i+2]
+		case s[i] == '[':
+			end := matchingBracket(s, i)
+			if end == -1 {
+				return prefix.String()
+			}
+			token = s[i : end+1]
+		default:
+			token = s[i : i+1]
+		}
+
+		next := i + len(token)
+		if isQuantified(s, next) {
+			break
+		}
+
+		// Only a plain literal or an escaped literal contributes.
+		switch {
+		case len(token) == 2 && token[0] == '\\' && !isEscapeClass(token[1]):
+			prefix.WriteByte(token[1])
+		case len(token) == 1 && !strings.ContainsAny(token, `.[]()^$*+?{}|`):
+			prefix.WriteByte(token[0])
+		default:
+			return prefix.String()
+		}
+
+		i = next
+	}
+
+	return prefix.String()
+}
+
+// hostIsOpen reports whether the authority part of the pattern can be left
+// without crossing a terminator, which means the pattern also matches
+// attacker-chosen suffix hosts or userinfo.
+//
+// It walks the tokens after "://" and classifies each one. A terminator ends
+// the authority, so the pattern is safe. A crosser can match "@", "?" or "#"
+// and therefore lets a matching URL escape the authority, so the pattern is
+// open. Reaching the end without a terminator is open too, which is the
+// classic "^https://trusted\.example\.com" case.
+func hostIsOpen(s string) bool {
+	_, after, ok := strings.Cut(s, "://")
+	if !ok {
+		// No authority to reason about, for example "^file:///tmp/".
+		return false
+	}
+
+	rest := after
+
+	for i := 0; i < len(rest); {
+		var token string
+		switch {
+		case rest[i] == '\\' && i+1 < len(rest):
+			token = rest[i : i+2]
+		case rest[i] == '[':
+			end := matchingBracket(rest, i)
+			if end == -1 {
+				return true
+			}
+			token = rest[i : end+1]
+		case rest[i] == '(':
+			end := matchingParen(rest, i)
+			if end == -1 {
+				return true
+			}
+			token = rest[i : end+1]
+		default:
+			token = rest[i : i+1]
+		}
+
+		next := i + len(token)
+		optional := isOptionalQuantifier(rest, next)
+
+		switch classifyHostToken(token) {
+		case hostTokenTerminator:
+			// An optional terminator does not end anything, since the URL may
+			// match without it.
+			if !optional {
+				return false
+			}
+		case hostTokenCrosser:
+			return true
+		case hostTokenNeutral:
+			// Part of the host itself, so keep walking.
+		}
+
+		i = next
+		for i < len(rest) && isQuantifierByte(rest[i]) {
+			if rest[i] == '{' {
+				end := strings.IndexByte(rest[i:], '}')
+				if end == -1 {
+					return true
+				}
+				i += end + 1
+				continue
+			}
+			i++
+		}
+	}
+
+	return true
+}
+
+// hostTokenKind is how a token affects the walk in [hostIsOpen].
+type hostTokenKind int
+
+const (
+	hostTokenNeutral hostTokenKind = iota
+	hostTokenTerminator
+	hostTokenCrosser
+)
+
+// hostTerminators are the characters that end the authority of a URL.
+const hostTerminators = "/:#?"
+
+// crosserClassChars are the characters that, if a class can match them, let a
+// match escape the authority. "/" is deliberately absent: it ends the
+// authority rather than escaping it, so a class such as "[:/]" is safe.
+const crosserClassChars = "@?#"
+
+// classifyHostToken classifies one token of the authority walk.
+func classifyHostToken(token string) hostTokenKind {
+	switch {
+	case token == ".":
+		// The wildcard matches "@", "#" and "?", so a host built on it can be
+		// left without ever reaching a terminator.
+		return hostTokenCrosser
+
+	case token == "$":
+		return hostTokenTerminator
+
+	case len(token) == 1 && strings.Contains(hostTerminators, token):
+		return hostTokenTerminator
+
+	case len(token) == 2 && token[0] == '\\':
+		switch token[1] {
+		case 'S', 'D', 'W':
+			return hostTokenCrosser
+		case 'd', 'w', 's':
+			return hostTokenNeutral
+		case 'p', 'P':
+			return hostTokenCrosser
+		}
+		if strings.Contains(hostTerminators, token[1:]) {
+			return hostTokenTerminator
+		}
+		return hostTokenNeutral
+
+	case strings.HasPrefix(token, "["):
+		inner := strings.TrimSuffix(strings.TrimPrefix(token, "["), "]")
+		if strings.HasPrefix(inner, "^") {
+			// A negated class almost always admits "@".
+			return hostTokenCrosser
+		}
+		if classContainsAny(inner, crosserClassChars) {
+			return hostTokenCrosser
+		}
+		if classOnlyTerminators(inner) {
+			return hostTokenTerminator
+		}
+		return hostTokenNeutral
+
+	case strings.HasPrefix(token, "("):
+		return classifyGroup(token)
+	}
+
+	return hostTokenNeutral
+}
+
+// classifyGroup classifies a parenthesized group. A group whose every branch
+// starts with a terminator ends the authority, which is what makes the
+// idiomatic "(:|/|$)" safe. A group containing a crosser is a crosser.
+func classifyGroup(token string) hostTokenKind {
+	inner := trimInlineFlags(strings.TrimSuffix(strings.TrimPrefix(token, "("), ")"))
+	inner = strings.TrimPrefix(inner, "?:")
+
+	branches := splitTopLevelAlternation(inner)
+
+	allTerminate := true
+	for _, branch := range branches {
+		if branch == "" {
+			allTerminate = false
+			continue
+		}
+
+		kind := classifyHostToken(firstToken(branch))
+		if kind == hostTokenCrosser {
+			return hostTokenCrosser
+		}
+		if kind != hostTokenTerminator {
+			allTerminate = false
+		}
+
+		// A crosser anywhere inside the branch still escapes the authority.
+		if branchHasCrosser(branch) {
+			return hostTokenCrosser
+		}
+	}
+
+	if allTerminate {
+		return hostTokenTerminator
+	}
+
+	return hostTokenNeutral
+}
+
+// branchHasCrosser reports whether any token of branch is a crosser.
+func branchHasCrosser(branch string) bool {
+	for i := 0; i < len(branch); {
+		token := tokenAt(branch, i)
+		if token == "" {
+			return true
+		}
+		if classifyHostToken(token) == hostTokenCrosser {
+			return true
+		}
+		i += len(token)
+	}
+
+	return false
+}
+
+// firstToken returns the first regex token of s.
+func firstToken(s string) string {
+	return tokenAt(s, 0)
+}
+
+// tokenAt returns the regex token starting at index i, or "" if it is
+// malformed.
+func tokenAt(s string, i int) string {
+	if i >= len(s) {
+		return ""
+	}
+
+	switch {
+	case s[i] == '\\' && i+1 < len(s):
+		return s[i : i+2]
+	case s[i] == '[':
+		end := matchingBracket(s, i)
+		if end == -1 {
+			return ""
+		}
+		return s[i : end+1]
+	case s[i] == '(':
+		end := matchingParen(s, i)
+		if end == -1 {
+			return ""
+		}
+		return s[i : end+1]
+	}
+
+	return s[i : i+1]
+}
+
+// classOnlyTerminators reports whether every character a class can match ends
+// the authority, which makes the class itself a terminator. A range is never
+// treated as one.
+func classOnlyTerminators(class string) bool {
+	if class == "" {
+		return false
+	}
+
+	for i := 0; i < len(class); i++ {
+		if class[i] == '\\' && i+1 < len(class) {
+			if !strings.Contains(hostTerminators, class[i+1:i+2]) {
+				return false
+			}
+			i++
+			continue
+		}
+
+		if i+2 < len(class) && class[i+1] == '-' {
+			return false
+		}
+
+		if !strings.Contains(hostTerminators, class[i:i+1]) {
+			return false
+		}
+	}
+
+	return true
+}
+
+// classContainsAny reports whether a character class body can match any of the
+// given characters, expanding simple ranges.
+func classContainsAny(class, chars string) bool {
+	for i := 0; i < len(class); i++ {
+		if class[i] == '\\' && i+1 < len(class) {
+			// An escape class such as \S inside a class admits everything.
+			if strings.ContainsRune("SDW", rune(class[i+1])) {
+				return true
+			}
+			if strings.ContainsRune(chars, rune(class[i+1])) {
+				return true
+			}
+			i++
+			continue
+		}
+
+		if i+2 < len(class) && class[i+1] == '-' {
+			lo, hi := class[i], class[i+2]
+			for _, c := range []byte(chars) {
+				if c >= lo && c <= hi {
+					return true
+				}
+			}
+			i += 2
+			continue
+		}
+
+		if strings.ContainsRune(chars, rune(class[i])) {
+			return true
+		}
+	}
+
+	return false
+}
+
+// matchingParen returns the index of the ")" closing the "(" at start.
+func matchingParen(s string, start int) int {
+	depth := 0
+	inClass := false
+
+	for i := start; i < len(s); i++ {
+		switch {
+		case s[i] == '\\' && i+1 < len(s):
+			i++
+		case s[i] == '[' && !inClass:
+			inClass = true
+		case s[i] == ']' && inClass:
+			inClass = false
+		case s[i] == '(' && !inClass:
+			depth++
+		case s[i] == ')' && !inClass:
+			depth--
+			if depth == 0 {
+				return i
+			}
+		}
+	}
+
+	return -1
+}
+
+// matchingBracket returns the index of the "]" closing the "[" at start.
+func matchingBracket(s string, start int) int {
+	for i := start + 1; i < len(s); i++ {
+		switch {
+		case s[i] == '\\' && i+1 < len(s):
+			i++
+		case s[i] == ']':
+			// A "]" immediately after "[" or "[^" is a literal.
+			if i == start+1 || (i == start+2 && s[start+1] == '^') {
+				continue
+			}
+			return i
+		}
+	}
+
+	return -1
+}
+
+// isQuantifierByte reports whether c opens a quantifier.
+func isQuantifierByte(c byte) bool {
+	return c == '?' || c == '*' || c == '+' || c == '{'
+}
+
+// isQuantified reports whether a quantifier starts at index i.
+func isQuantified(s string, i int) bool {
+	return i < len(s) && isQuantifierByte(s[i])
+}
+
+// isOptionalQuantifier reports whether the quantifier at index i lets the
+// preceding token match nothing.
+func isOptionalQuantifier(s string, i int) bool {
+	if i >= len(s) {
+		return false
+	}
+
+	switch s[i] {
+	case '?', '*':
+		return true
+	case '{':
+		return strings.HasPrefix(s[i:], "{0")
+	}
+
+	return false
+}
+
+// isEscapeClass reports whether c after a backslash denotes a character class
+// rather than a literal.
+func isEscapeClass(c byte) bool {
+	return strings.ContainsRune("dDwWsSbBAzZpP", rune(c))
+}
+
+// commonPrefix returns the longest common prefix of a and b.
+func commonPrefix(a, b string) string {
+	n := min(len(a), len(b))
+	for i := range n {
+		if a[i] != b[i] {
+			return a[:i]
+		}
+	}
+
+	return a[:n]
+}

pkg/gotenberg/allowlist_test.go

@@ -0,0 +1,179 @@
+package gotenberg
+
+import (
+	"testing"
+
+	"github.com/dlclark/regexp2/v2"
+)
+
+func TestAuditAllowList(t *testing.T) {
+	for _, tc := range []struct {
+		scenario string
+		pattern  string
+		want     AllowListRisk
+	}{
+		// Safe: the host is terminated before anything can leave it.
+		{"idiomatic terminator group", `^https?://internal\.svc(:|/|$)`, ""},
+		{"trailing slash", `^https://trusted\.example\.com/`, ""},
+		{"optional port then terminator", `^https://example\.com(:[0-9]+)?(/|$)`, ""},
+		{"positive class cannot leave authority", `^https://[a-z0-9.-]+\.s3\.amazonaws\.com/`, ""},
+		{"leading mandatory group", `^(https|http)://a\.example\.com/`, ""},
+		{"optional subdomain group", `^https://(www\.)?example\.com/`, ""},
+		{"port terminator", `^https://example\.com:8443/`, ""},
+		{"end anchor", `^https://example\.com$`, ""},
+		{"alternation both anchored and terminated", `^https://a\.example/|^https://b\.example/`, ""},
+		{"no authority to check", `^file:///tmp/`, ""},
+		{"digit class in host", `^https://node\d+\.example\.com/`, ""},
+		{"class of only terminators", `^https://example\.com[:/]`, ""},
+		{"feature file pattern, fixed", `^https?://host\.docker\.internal(:[0-9]+)?/`, ""},
+
+		// Unanchored: regexp2 searches, so these match anywhere in the URL.
+		{"no anchor", `trusted\.example\.com`, AllowListRiskUnanchored},
+		{"no anchor with scheme", `https://trusted\.example\.com/`, AllowListRiskUnanchored},
+
+		// Only the first branch anchored.
+		{"second branch unanchored", `^http://a\.example/|http://b\.example/`, AllowListRiskUnanchoredBranch},
+
+		// Catch-all: matches every URL.
+		{"dot plus", `.+`, AllowListRiskCatchAll},
+		{"dot star", `.*`, AllowListRiskCatchAll},
+		{"anchored dot star", `^.*`, AllowListRiskCatchAll},
+		{"anchored dot plus", `^.+`, AllowListRiskCatchAll},
+
+		// Open host: the reported vulnerability class.
+		{"advisory pattern", `^http://trusted\.example\.com`, AllowListRiskOpenHost},
+		{"gotenberg.dev internet-facing recipe", `^https?://[^/]+\.internal\.example\.com`, AllowListRiskOpenHost},
+		{"gotenberg.dev strict whitelist recipe", `^https://(api|cdn|images)\.internal\.example\.com`, AllowListRiskOpenHost},
+		{"gotenberg.dev hooks recipe", `^https?://hooks\.internal\.example\.com`, AllowListRiskOpenHost},
+		{"feature file pattern", `^https?://host.docker.internal.*`, AllowListRiskOpenHost},
+		{"scheme only", `^https?://`, AllowListRiskOpenHost},
+		{"wildcard subdomain", `^https://.+\.example\.com/`, AllowListRiskOpenHost},
+		{"escaped dot is not a terminator", `^https?://example\.com\.`, AllowListRiskOpenHost},
+		{"negated class in host", `^https://[^.]+\.example\.com/`, AllowListRiskOpenHost},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			findings := AuditAllowList([]string{tc.pattern})
+
+			if tc.want == "" {
+				if len(findings) != 0 {
+					t.Fatalf("AuditAllowList(%q) = %+v, want no finding", tc.pattern, findings)
+				}
+				return
+			}
+
+			if len(findings) != 1 {
+				t.Fatalf("AuditAllowList(%q) returned %d findings, want 1", tc.pattern, len(findings))
+			}
+			if findings[0].Risk != tc.want {
+				t.Fatalf("AuditAllowList(%q) risk = %q, want %q", tc.pattern, findings[0].Risk, tc.want)
+			}
+		})
+	}
+}
+
+// TestAuditAllowList_FlaggedPatternsAreActuallyExploitable proves the audit is
+// not merely syntactic: every pattern it flags as open-host really does admit
+// a host the operator did not intend.
+func TestAuditAllowList_FlaggedPatternsAreActuallyExploitable(t *testing.T) {
+	for _, tc := range []struct {
+		pattern string
+		attack  string
+	}{
+		{`^http://trusted\.example\.com`, "http://trusted.example.com.attacker.example/"},
+		{`^https?://[^/]+\.internal\.example\.com`, "http://a.internal.example.com.attacker.example/"},
+		{`^https://(api|cdn|images)\.internal\.example\.com`, "https://api.internal.example.com.attacker.example/"},
+		{`^https?://hooks\.internal\.example\.com`, "http://hooks.internal.example.com.attacker.example/"},
+		{`^https?://host.docker.internal.*`, "http://host.docker.internal.attacker.example/"},
+		{`^https://.+\.example\.com/`, "https://attacker.example/#x.example.com/"},
+		{`^https?://example\.com\.`, "http://example.com.attacker.example/"},
+	} {
+		t.Run(tc.pattern, func(t *testing.T) {
+			findings := AuditAllowList([]string{tc.pattern})
+			if len(findings) == 0 {
+				t.Fatalf("pattern %q was not flagged", tc.pattern)
+			}
+
+			ok, err := regexp2.MustCompile(tc.pattern, regexp2.None).MatchString(tc.attack)
+			if err != nil {
+				t.Fatalf("match %q: %v", tc.attack, err)
+			}
+			if !ok {
+				t.Fatalf("pattern %q does not match %q, so the finding is a false positive", tc.pattern, tc.attack)
+			}
+		})
+	}
+}
+
+// TestAuditAllowList_SafePatternsRejectTheAttacks is the converse: the shapes
+// the audit stays silent about really do reject the same attacks.
+func TestAuditAllowList_SafePatternsRejectTheAttacks(t *testing.T) {
+	safe := []string{
+		`^https?://internal\.svc(:|/|$)`,
+		`^https://trusted\.example\.com/`,
+		`^https://example\.com(:[0-9]+)?(/|$)`,
+		`^https://[a-z0-9.-]+\.s3\.amazonaws\.com/`,
+	}
+	attacks := []string{
+		"https://internal.svc.attacker.example/",
+		"https://trusted.example.com.attacker.example/",
+		"https://trusted.example.com@169.254.169.254/",
+		"https://example.com.attacker.example/",
+		"https://example.com@10.0.0.5/",
+		"https://bucket.s3.amazonaws.com.attacker.example/",
+		"https://bucket.s3.amazonaws.com@127.0.0.1/",
+	}
+
+	for _, pattern := range safe {
+		t.Run(pattern, func(t *testing.T) {
+			if findings := AuditAllowList([]string{pattern}); len(findings) != 0 {
+				t.Fatalf("safe pattern %q was flagged as %q", pattern, findings[0].Risk)
+			}
+
+			re := regexp2.MustCompile(pattern, regexp2.None)
+			for _, attack := range attacks {
+				ok, err := re.MatchString(attack)
+				if err != nil {
+					t.Fatalf("match %q: %v", attack, err)
+				}
+				if ok {
+					t.Fatalf("pattern %q matches attack %q but was not flagged", pattern, attack)
+				}
+			}
+		})
+	}
+}
+
+func TestAuditAllowList_SkipsEmptyAndOversized(t *testing.T) {
+	oversized := make([]byte, maxAuditedPatternLength+1)
+	for i := range oversized {
+		oversized[i] = 'a'
+	}
+
+	findings := AuditAllowList([]string{"", string(oversized)})
+	if len(findings) != 0 {
+		t.Fatalf("AuditAllowList returned %+v, want no finding", findings)
+	}
+}
+
+func TestAuditAllowList_ReportsIndex(t *testing.T) {
+	findings := AuditAllowList([]string{
+		`^https://ok\.example\.com/`,
+		`^https://open\.example\.com`,
+	})
+	if len(findings) != 1 {
+		t.Fatalf("got %d findings, want 1", len(findings))
+	}
+	if findings[0].Index != 1 {
+		t.Fatalf("findings[0].Index = %d, want 1", findings[0].Index)
+	}
+}
+
+// TestAuditAllowList_ShippedChromiumDenyListIsNotAudited guards the rule that
+// deny-lists are never audited. The shipped Chromium deny-list uses a
+// lookaround and has no authority, so auditing it would produce noise.
+func TestAuditAllowList_LookaroundIsNotFlaggedForHost(t *testing.T) {
+	findings := AuditAllowList([]string{`^file:(?!//\/tmp/).*`})
+	if len(findings) != 0 {
+		t.Fatalf("AuditAllowList returned %+v, want no finding", findings)
+	}
+}

pkg/gotenberg/filter.go

@@ -1,70 +0,0 @@
-package gotenberg
-
-import (
-	"context"
-	"errors"
-	"fmt"
-	"time"
-
-	"github.com/dlclark/regexp2"
-)
-
-// ErrFiltered happens if a value is filtered by the [FilterDeadline] function.
-var ErrFiltered = errors.New("value filtered")
-
-// FilterDeadline checks if the given value is allowed and not denied according
-// to regex patterns. The allowed list uses OR semantics (value must match at
-// least one pattern). The denied list uses OR semantics (value is denied if it
-// matches any pattern). It returns a [context.DeadlineExceeded] if it takes
-// too long to process.
-func FilterDeadline(allowed, denied []*regexp2.Regexp, s string, deadline time.Time) error {
-	if len(allowed) > 0 {
-		matched := false
-
-		for _, pattern := range allowed {
-			// FIXME: not ideal to compile everytime, but is there another way to create a clone?
-			clone := regexp2.MustCompile(pattern.String(), 0)
-			clone.MatchTimeout = time.Until(deadline)
-
-			ok, err := clone.MatchString(s)
-			if err != nil {
-				if time.Now().After(deadline) {
-					return context.DeadlineExceeded
-				}
-
-				return fmt.Errorf("'%s' cannot handle '%s': %w", clone.String(), s, err)
-			}
-
-			if ok {
-				matched = true
-				break
-			}
-		}
-
-		if !matched {
-			return fmt.Errorf("'%s' does not match any expression from the allowed list: %w", s, ErrFiltered)
-		}
-	}
-
-	if len(denied) > 0 {
-		for _, pattern := range denied {
-			clone := regexp2.MustCompile(pattern.String(), 0)
-			clone.MatchTimeout = time.Until(deadline)
-
-			ok, err := clone.MatchString(s)
-			if err != nil {
-				if time.Now().After(deadline) {
-					return context.DeadlineExceeded
-				}
-
-				return fmt.Errorf("'%s' cannot handle '%s': %w", clone.String(), s, err)
-			}
-
-			if ok {
-				return fmt.Errorf("'%s' matches the expression from the denied list: %w", s, ErrFiltered)
-			}
-		}
-	}
-
-	return nil
-}

pkg/gotenberg/filter_test.go

@@ -1,117 +0,0 @@
-package gotenberg
-
-import (
-	"context"
-	"errors"
-	"testing"
-	"time"
-
-	"github.com/dlclark/regexp2"
-)
-
-func TestFilterDeadline(t *testing.T) {
-	for _, tc := range []struct {
-		scenario      string
-		allowed       []*regexp2.Regexp
-		denied        []*regexp2.Regexp
-		s             string
-		deadline      time.Time
-		expectError   bool
-		expectedError error
-	}{
-		{
-			scenario:      "DeadlineExceeded (allowed)",
-			allowed:       []*regexp2.Regexp{regexp2.MustCompile("foo", 0)},
-			denied:        nil,
-			s:             "foo",
-			deadline:      time.Now().Add(time.Duration(-1) * time.Hour),
-			expectError:   true,
-			expectedError: context.DeadlineExceeded,
-		},
-		{
-			scenario:      "ErrFiltered (allowed, no match)",
-			allowed:       []*regexp2.Regexp{regexp2.MustCompile("foo", 0)},
-			denied:        nil,
-			s:             "bar",
-			deadline:      time.Now().Add(time.Duration(5) * time.Second),
-			expectError:   true,
-			expectedError: ErrFiltered,
-		},
-		{
-			scenario:      "DeadlineExceeded (denied)",
-			allowed:       nil,
-			denied:        []*regexp2.Regexp{regexp2.MustCompile("foo", 0)},
-			s:             "foo",
-			deadline:      time.Now().Add(time.Duration(-1) * time.Hour),
-			expectError:   true,
-			expectedError: context.DeadlineExceeded,
-		},
-		{
-			scenario:      "ErrFiltered (denied)",
-			allowed:       nil,
-			denied:        []*regexp2.Regexp{regexp2.MustCompile("foo", 0)},
-			s:             "foo",
-			deadline:      time.Now().Add(time.Duration(5) * time.Second),
-			expectError:   true,
-			expectedError: ErrFiltered,
-		},
-		{
-			scenario:    "success (empty lists)",
-			allowed:     nil,
-			denied:      nil,
-			s:           "foo",
-			deadline:    time.Now().Add(time.Duration(5) * time.Second),
-			expectError: false,
-		},
-		{
-			scenario:    "multi-pattern allow list, second matches",
-			allowed:     []*regexp2.Regexp{regexp2.MustCompile("^https://", 0), regexp2.MustCompile("^file:///tmp/", 0)},
-			denied:      nil,
-			s:           "file:///tmp/abc/index.html",
-			deadline:    time.Now().Add(time.Duration(5) * time.Second),
-			expectError: false,
-		},
-		{
-			scenario:      "multi-pattern allow list, none matches",
-			allowed:       []*regexp2.Regexp{regexp2.MustCompile("^https://", 0), regexp2.MustCompile("^ftp://", 0)},
-			denied:        nil,
-			s:             "file:///tmp/abc/index.html",
-			deadline:      time.Now().Add(time.Duration(5) * time.Second),
-			expectError:   true,
-			expectedError: ErrFiltered,
-		},
-		{
-			scenario:      "multi-pattern deny list, second matches",
-			allowed:       nil,
-			denied:        []*regexp2.Regexp{regexp2.MustCompile("^ftp://", 0), regexp2.MustCompile("^file:.*", 0)},
-			s:             "file:///etc/passwd",
-			deadline:      time.Now().Add(time.Duration(5) * time.Second),
-			expectError:   true,
-			expectedError: ErrFiltered,
-		},
-		{
-			scenario:    "https URL passes deny list targeting file://",
-			allowed:     nil,
-			denied:      []*regexp2.Regexp{regexp2.MustCompile("^file:.*", 0)},
-			s:           "https://example.com",
-			deadline:    time.Now().Add(time.Duration(5) * time.Second),
-			expectError: false,
-		},
-	} {
-		t.Run(tc.scenario, func(t *testing.T) {
-			err := FilterDeadline(tc.allowed, tc.denied, tc.s, tc.deadline)
-
-			if tc.expectError && err == nil {
-				t.Fatal("expected an error but got none")
-			}
-
-			if !tc.expectError && err != nil {
-				t.Fatalf("expected no error but got: %v", err)
-			}
-
-			if tc.expectedError != nil && !errors.Is(err, tc.expectedError) {
-				t.Fatalf("expected error %v but got: %v", tc.expectedError, err)
-			}
-		})
-	}
-}

pkg/gotenberg/flags.go

@@ -1,11 +1,17 @@
 package gotenberg
 
 import (
+	"context"
+	"fmt"
+	"log/slog"
+	"strings"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"github.com/labstack/gommon/bytes"
 	flag "github.com/spf13/pflag"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg/internal/log"
 )
 
 // ParsedFlags wraps a [flag.FlagSet] so that retrieving the typed values is
@@ -201,15 +207,42 @@ func (f *ParsedFlags) MustDeprecatedHumanReadableBytes(deprecated string, newNam
 	return f.MustHumanReadableBytes(newName)
 }
 
+// PatternMatchTimeout bounds a single match against an operator-supplied
+// allow-list or deny-list pattern.
+//
+// regexp2 backtracks, and the strings matched against these patterns are
+// client-controlled: a request URL, a CONNECT host. A pattern that backtracks
+// catastrophically would otherwise burn a core for as long as the caller's
+// deadline allows, which is --api-timeout (env API_TIMEOUT), 30 seconds by
+// default. The ceiling mirrors the one the Chromium module already applies to
+// the per-request extraHttpHeaders scope pattern.
+//
+// [ParsedFlags.MustRegexp] and [ParsedFlags.MustRegexpSlice] stamp this onto
+// every pattern they compile, which is how all four production lists are
+// built. Patterns compiled any other way keep regexp2's default of
+// math.MaxInt64, which it treats as no timeout at all, so a hand-built slice
+// must set this itself before reaching [DecideOutbound].
+//
+// The ceiling is wall-clock. Match through [MatchPattern] rather than calling
+// regexp2 directly: a match that never approaches the ceiling still aborts if
+// the process loses the CPU at the wrong moment.
+const PatternMatchTimeout = 250 * time.Millisecond
+
 // MustRegexp returns the regular expression of a flag given by name.
 // It panics if an error occurs.
+//
+// The returned expression carries [PatternMatchTimeout] and is safe to match
+// on concurrently: callers must not compile a private copy per match.
 func (f *ParsedFlags) MustRegexp(name string) *regexp2.Regexp {
 	val, err := f.GetString(name)
 	if err != nil {
 		panic(err)
 	}
 
-	return regexp2.MustCompile(val, 0)
+	re := regexp2.MustCompile(val, regexp2.None)
+	re.MatchTimeout = PatternMatchTimeout
+
+	return re
 }
 
 // MustDeprecatedRegexp returns the regular expression of a deprecated flag if
@@ -226,21 +259,140 @@ func (f *ParsedFlags) MustDeprecatedRegexp(deprecated string, newName string) *r
 // MustRegexpSlice returns a slice of compiled regular expressions from a
 // string-slice flag given by name. Empty strings are skipped.
 // It panics if an error occurs.
+//
+// Every allow-list and deny-list in Gotenberg is read through this method, so
+// it is also where allow-list patterns are audited. See [AuditAllowList].
+//
+// The returned expressions carry [PatternMatchTimeout] and are safe to match
+// on concurrently: callers must not compile a private copy per match.
 func (f *ParsedFlags) MustRegexpSlice(name string) []*regexp2.Regexp {
 	vals := f.MustStringSlice(name)
 
+	f.warnRiskyAllowList(name, vals)
+
 	var regexps []*regexp2.Regexp
 	for _, val := range vals {
 		if val == "" {
 			continue
 		}
 
-		regexps = append(regexps, regexp2.MustCompile(val, 0))
+		re := regexp2.MustCompile(val, regexp2.None)
+		re.MatchTimeout = PatternMatchTimeout
+
+		regexps = append(regexps, re)
 	}
 
 	return regexps
 }
 
+// allowListFlagSuffix identifies the flags whose patterns grant an IP-check
+// bypass. Deny-lists are never audited: they always apply, cannot be bypassed,
+// and a loose deny-list is safe rather than dangerous.
+const allowListFlagSuffix = "-allow-list"
+
+// warnRiskyAllowList logs one warning per allow-list entry that matches more
+// URLs than its author is likely to intend.
+//
+// It warns and never fails: operators depend on loose patterns today, and
+// rejecting them at startup would break running deployments.
+func (f *ParsedFlags) warnRiskyAllowList(name string, vals []string) {
+	if !strings.HasSuffix(name, allowListFlagSuffix) {
+		return
+	}
+
+	findings := AuditAllowList(vals)
+	if len(findings) == 0 {
+		return
+	}
+
+	// The logger is nil until the entry point initializes it, which happens
+	// before any module is provisioned. Tests and embedders that call this
+	// method directly get no logger, and must not panic for it.
+	logger := log.Logger()
+	if logger == nil {
+		return
+	}
+
+	for _, finding := range findings {
+		// Provision has no context.Context to propagate, so the trace-aware
+		// logging convention is satisfied with a background context.
+		logger.WarnContext(
+			context.Background(),
+			f.allowListWarning(name, finding),
+			slog.String("flag", "--"+name),
+			slog.String("env", EnvVarName(name)),
+			slog.Int("entry", finding.Index+1),
+			slog.String("reason", string(finding.Risk)),
+		)
+	}
+}
+
+// allowListWarning builds the operator-facing message for a finding. It names
+// the flag and its environment variable, and, when they exist, the IP-check
+// flags the entry silently disables.
+func (f *ParsedFlags) allowListWarning(name string, finding AllowListFinding) string {
+	var b strings.Builder
+
+	// Print the pattern raw rather than quoted: %q escapes every backslash, so
+	// the operator would not recognize the value they set.
+	fmt.Fprintf(&b, "--%s (%s) entry %d '%s' ", name, EnvVarName(name), finding.Index+1, finding.Pattern)
+
+	switch finding.Risk {
+	case AllowListRiskUnanchored:
+		b.WriteString("is not anchored with ^, so it matches anywhere in the URL and a URL such as http://attacker.example/?u=trusted.example.com passes. ")
+	case AllowListRiskUnanchoredBranch:
+		b.WriteString("has an alternation branch that is not anchored with ^, and that branch matches anywhere in the URL. ")
+	case AllowListRiskCatchAll:
+		b.WriteString("matches every URL. ")
+	case AllowListRiskOpenHost:
+		b.WriteString("does not terminate the host, so it also matches suffix hosts such as http://trusted.example.com.attacker.example/. ")
+	}
+
+	b.WriteString(f.bypassSentence(name))
+
+	switch finding.Risk {
+	case AllowListRiskUnanchored, AllowListRiskUnanchoredBranch:
+		b.WriteString("Anchor every branch with ^ and end the host with /, :, or $.")
+	case AllowListRiskCatchAll:
+		b.WriteString("Restrict the entry to the hosts you trust, or unset the flag.")
+	case AllowListRiskOpenHost:
+		b.WriteString("End the host with /, :, $, or a group such as (:|/|$).")
+	}
+
+	return b.String()
+}
+
+// bypassSentence names the IP-check flags an allow-list match skips, when the
+// module registers them.
+func (f *ParsedFlags) bypassSentence(name string) string {
+	prefix := strings.TrimSuffix(name, allowListFlagSuffix)
+
+	private, public := prefix+"-deny-private-ips", prefix+"-deny-public-ips"
+	if f.Lookup(private) == nil || f.Lookup(public) == nil {
+		// A deprecated alias such as webhook-error-allow-list carries an extra
+		// segment that the IP-check flags do not have.
+		if i := strings.LastIndex(prefix, "-"); i != -1 {
+			private, public = prefix[:i]+"-deny-private-ips", prefix[:i]+"-deny-public-ips"
+		}
+	}
+
+	if f.Lookup(private) == nil || f.Lookup(public) == nil {
+		return "A URL that matches the allow-list skips the private and public IP checks. "
+	}
+
+	return fmt.Sprintf(
+		"A URL that matches the allow-list skips --%s (%s) and --%s (%s). ",
+		private, EnvVarName(private), public, EnvVarName(public),
+	)
+}
+
+// EnvVarName returns the environment variable that overrides the flag given by
+// name. The entry point derives the same name when it applies environment
+// overrides, so operator-facing messages can name both without drifting.
+func EnvVarName(name string) string {
+	return strings.ToUpper(strings.ReplaceAll(name, "-", "_"))
+}
+
 // MustDeprecatedRegexpSlice returns the slice of compiled regular expressions
 // of a deprecated flag if it was explicitly set or the slice of the new flag.
 // It panics if an error occurs.

pkg/gotenberg/flags_test.go

@@ -3,10 +3,11 @@ package gotenberg
 import (
 	"reflect"
 	"regexp"
+	"strings"
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	flag "github.com/spf13/pflag"
 )
 
@@ -951,3 +952,138 @@ func TestParsedFlags_MustDeprecatedRegexpSlice(t *testing.T) {
 
 	_ = regexp2.None // Keep import alive.
 }
+
+func TestParsedFlags_AllowListWarning(t *testing.T) {
+	fs := flag.NewFlagSet("tests", flag.ContinueOnError)
+	fs.StringSlice("chromium-allow-list", []string{}, "")
+	fs.Bool("chromium-deny-private-ips", false, "")
+	fs.Bool("chromium-deny-public-ips", false, "")
+	fs.StringSlice("standalone-allow-list", []string{}, "")
+
+	parsedFlags := ParsedFlags{FlagSet: fs}
+
+	for _, tc := range []struct {
+		scenario string
+		name     string
+		finding  AllowListFinding
+		contains []string
+	}{
+		{
+			scenario: "open host names both IP-check flags and their env vars",
+			name:     "chromium-allow-list",
+			finding:  AllowListFinding{Index: 0, Pattern: `^https://trusted\.example\.com`, Risk: AllowListRiskOpenHost},
+			contains: []string{
+				"--chromium-allow-list (CHROMIUM_ALLOW_LIST)",
+				"entry 1",
+				`^https://trusted\.example\.com`,
+				"does not terminate the host",
+				"--chromium-deny-private-ips (CHROMIUM_DENY_PRIVATE_IPS)",
+				"--chromium-deny-public-ips (CHROMIUM_DENY_PUBLIC_IPS)",
+				"End the host with",
+			},
+		},
+		{
+			scenario: "catch-all tells the operator to restrict or unset",
+			name:     "chromium-allow-list",
+			finding:  AllowListFinding{Index: 2, Pattern: ".+", Risk: AllowListRiskCatchAll},
+			contains: []string{"entry 3", "matches every URL", "Restrict the entry"},
+		},
+		{
+			scenario: "unanchored explains the search semantics",
+			name:     "chromium-allow-list",
+			finding:  AllowListFinding{Index: 0, Pattern: `trusted\.example\.com`, Risk: AllowListRiskUnanchored},
+			contains: []string{"is not anchored with ^", "Anchor every branch with ^"},
+		},
+		{
+			scenario: "module without IP-check flags falls back to a generic sentence",
+			name:     "standalone-allow-list",
+			finding:  AllowListFinding{Index: 0, Pattern: `^https://a\.example\.com`, Risk: AllowListRiskOpenHost},
+			contains: []string{"skips the private and public IP checks"},
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			msg := parsedFlags.allowListWarning(tc.name, tc.finding)
+
+			for _, want := range tc.contains {
+				if !strings.Contains(msg, want) {
+					t.Fatalf("message %q does not contain %q", msg, want)
+				}
+			}
+			if strings.Contains(msg, "—") {
+				t.Fatalf("message must not contain an em dash: %q", msg)
+			}
+		})
+	}
+}
+
+func TestParsedFlags_WarnRiskyAllowList_SkipsDenyLists(t *testing.T) {
+	fs := flag.NewFlagSet("tests", flag.ContinueOnError)
+	fs.StringSlice("chromium-deny-list", []string{}, "")
+
+	parsedFlags := ParsedFlags{FlagSet: fs}
+
+	// A deny-list is never audited: it always applies and cannot be bypassed,
+	// so a loose one is safe. This must also not panic on a nil logger.
+	parsedFlags.warnRiskyAllowList("chromium-deny-list", []string{".+", `^file:(?!//\/tmp/).*`})
+}
+
+func TestParsedFlags_WarnRiskyAllowList_NilLoggerDoesNotPanic(t *testing.T) {
+	fs := flag.NewFlagSet("tests", flag.ContinueOnError)
+	fs.StringSlice("chromium-allow-list", []string{}, "")
+
+	parsedFlags := ParsedFlags{FlagSet: fs}
+
+	// Provision runs after the entry point initializes the logger, but tests
+	// and embedders reach this path with no logger at all.
+	parsedFlags.warnRiskyAllowList("chromium-allow-list", []string{".+"})
+}
+
+func TestEnvVarName(t *testing.T) {
+	for _, tc := range []struct {
+		name string
+		want string
+	}{
+		{"chromium-allow-list", "CHROMIUM_ALLOW_LIST"},
+		{"api-download-from-deny-private-ips", "API_DOWNLOAD_FROM_DENY_PRIVATE_IPS"},
+		{"log-level", "LOG_LEVEL"},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := EnvVarName(tc.name); got != tc.want {
+				t.Fatalf("EnvVarName(%q) = %q, want %q", tc.name, got, tc.want)
+			}
+		})
+	}
+}
+
+func TestParsedFlags_RegexpMatchTimeout(t *testing.T) {
+	// [DecideOutbound] matches on these patterns directly instead of compiling
+	// a private copy per call, so the bound has to come from here. regexp2's
+	// own default is math.MaxInt64, which it treats as no
+	// timeout at all, so a pattern built without this stamp runs unbounded
+	// against a client-controlled string.
+	fs := flag.NewFlagSet("tests", flag.ContinueOnError)
+	fs.StringSlice("some-deny-list", []string{`^file:`, `^https?://`}, "")
+	fs.String("some-pattern", `^file:`, "")
+
+	err := fs.Parse(nil)
+	if err != nil {
+		t.Fatalf("expected no error but got: %v", err)
+	}
+
+	parsedFlags := ParsedFlags{FlagSet: fs}
+
+	regexps := parsedFlags.MustRegexpSlice("some-deny-list")
+	if len(regexps) != 2 {
+		t.Fatalf("expected 2 patterns but got %d", len(regexps))
+	}
+
+	for _, re := range regexps {
+		if re.MatchTimeout != PatternMatchTimeout {
+			t.Fatalf("pattern '%s' has MatchTimeout %s, expected %s", re.String(), re.MatchTimeout, PatternMatchTimeout)
+		}
+	}
+
+	if got := parsedFlags.MustRegexp("some-pattern").MatchTimeout; got != PatternMatchTimeout {
+		t.Fatalf("expected MustRegexp MatchTimeout %s but got %s", PatternMatchTimeout, got)
+	}
+}

pkg/gotenberg/internal/otel/otel.go

@@ -5,6 +5,7 @@ import (
 	"fmt"
 	"log/slog"
 	"os"
+	"strings"
 	"sync/atomic"
 
 	"go.opentelemetry.io/contrib/bridges/otelslog"
@@ -74,6 +75,24 @@ func buildResource(ctx context.Context, logger *slog.Logger, serviceName, servic
 	return merged
 }
 
+// OTEL_*_EXPORTER select the exporter for each signal. autoexport treats an
+// unset or empty value as a request for the OTLP exporter, which then fails
+// against the default localhost:4318 endpoint when nothing listens there and,
+// for metrics, keeps retrying on the periodic reader's timer. Gotenberg keeps
+// telemetry opt-in: a signal with no exporter configured is built without one
+// and stays inert. See https://github.com/gotenberg/gotenberg/issues/1643.
+const (
+	tracesExporterEnvKey  = "OTEL_TRACES_EXPORTER"
+	metricsExporterEnvKey = "OTEL_METRICS_EXPORTER"
+	logsExporterEnvKey    = "OTEL_LOGS_EXPORTER"
+)
+
+// exporterConfigured reports whether the operator selected an exporter for the
+// signal owning envKey. An unset or blank value keeps that signal off.
+func exporterConfigured(envKey string) bool {
+	return strings.TrimSpace(os.Getenv(envKey)) != ""
+}
+
 // InitTracerProvider initializes the OpenTelemetry tracer provider.
 func InitTracerProvider(logger *slog.Logger, serviceName, serviceVersion string) (shutdown func(context.Context) error, err error) {
 	initOtelLogger(logger)
@@ -86,13 +105,14 @@ func InitTracerProvider(logger *slog.Logger, serviceName, serviceVersion string)
 		trace.WithResource(res),
 	}
 
-	traceExporter, err := autoexport.NewSpanExporter(ctx)
-	if err != nil {
-		return nil, err
-	}
-
-	if !autoexport.IsNoneSpanExporter(traceExporter) {
-		traceOpts = append(traceOpts, trace.WithBatcher(traceExporter))
+	if exporterConfigured(tracesExporterEnvKey) {
+		traceExporter, err := autoexport.NewSpanExporter(ctx)
+		if err != nil {
+			return nil, err
+		}
+		if !autoexport.IsNoneSpanExporter(traceExporter) {
+			traceOpts = append(traceOpts, trace.WithBatcher(traceExporter))
+		}
 	}
 
 	traceProvider := trace.NewTracerProvider(traceOpts...)
@@ -119,13 +139,14 @@ func InitMeterProvider(logger *slog.Logger, serviceName, serviceVersion string)
 	}
 	metricOpts = append(metricOpts, exemplarFilterOptions()...)
 
-	metricReader, err := autoexport.NewMetricReader(ctx)
-	if err != nil {
-		return nil, err
-	}
-
-	if !autoexport.IsNoneMetricReader(metricReader) {
-		metricOpts = append(metricOpts, metric.WithReader(metricReader))
+	if exporterConfigured(metricsExporterEnvKey) {
+		metricReader, err := autoexport.NewMetricReader(ctx)
+		if err != nil {
+			return nil, err
+		}
+		if !autoexport.IsNoneMetricReader(metricReader) {
+			metricOpts = append(metricOpts, metric.WithReader(metricReader))
+		}
 	}
 
 	meterProvider := metric.NewMeterProvider(metricOpts...)
@@ -157,13 +178,14 @@ func InitLoggerProvider(logger *slog.Logger, serviceName, serviceVersion string)
 		log.WithResource(res),
 	}
 
-	logExporter, err := autoexport.NewLogExporter(ctx)
-	if err != nil {
-		return nil, nil, err
-	}
-
-	if !autoexport.IsNoneLogExporter(logExporter) {
-		logOpts = append(logOpts, log.WithProcessor(log.NewBatchProcessor(logExporter)))
+	if exporterConfigured(logsExporterEnvKey) {
+		logExporter, err := autoexport.NewLogExporter(ctx)
+		if err != nil {
+			return nil, nil, err
+		}
+		if !autoexport.IsNoneLogExporter(logExporter) {
+			logOpts = append(logOpts, log.WithProcessor(log.NewBatchProcessor(logExporter)))
+		}
 	}
 
 	loggerProvider := log.NewLoggerProvider(logOpts...)

pkg/gotenberg/internal/otel/otel_test.go

@@ -89,6 +89,49 @@ func TestInitTracerProvider_HonorsSamplerEnv(t *testing.T) {
 	}
 }
 
+// TestExporterConfigured pins the opt-in gate: an unset or blank
+// OTEL_*_EXPORTER keeps the signal off, so Gotenberg never wires the OTLP
+// exporter that autoexport would otherwise default to and fail to reach at
+// localhost:4318. See https://github.com/gotenberg/gotenberg/issues/1643.
+func TestExporterConfigured(t *testing.T) {
+	const key = "OTEL_METRICS_EXPORTER"
+
+	orig, had := os.LookupEnv(key)
+	t.Cleanup(func() {
+		if had {
+			os.Setenv(key, orig)
+			return
+		}
+		os.Unsetenv(key)
+	})
+
+	for _, tc := range []struct {
+		scenario string
+		unset    bool
+		value    string
+		want     bool
+	}{
+		{"unset", true, "", false},
+		{"empty", false, "", false},
+		{"whitespace only", false, "   ", false},
+		{"none", false, "none", true},
+		{"otlp", false, "otlp", true},
+		{"padded value", false, "  otlp  ", true},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			if tc.unset {
+				os.Unsetenv(key)
+			} else {
+				os.Setenv(key, tc.value)
+			}
+
+			if got := exporterConfigured(key); got != tc.want {
+				t.Errorf("exporterConfigured(%q) = %v, want %v", key, got, tc.want)
+			}
+		})
+	}
+}
+
 func TestExemplarFilterOptions(t *testing.T) {
 	t.Run("default pins trace-based", func(t *testing.T) {
 		if v, ok := os.LookupEnv("OTEL_METRICS_EXEMPLAR_FILTER"); ok {

pkg/gotenberg/outbound.go

@@ -15,7 +15,8 @@ import (
 	"strings"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
+	"github.com/hashicorp/go-retryablehttp"
 	"golang.org/x/net/http/httpproxy"
 )
 
@@ -26,6 +27,12 @@ import (
 // example [::ffff:127.0.0.1]).
 var ErrNonPublicIP = errors.New("non-public IP")
 
+// ErrFiltered happens when a value is rejected by an allow-list or a
+// deny-list, or when it cannot be validated and [DecideOutbound] fails closed.
+// Callers map it to a generic 403: the specific reason stays in the operator
+// logs so a client cannot probe the lists.
+var ErrFiltered = errors.New("value filtered")
+
 // ErrPublicIP indicates that an outbound URL targets an IP address that is
 // reachable on the public internet. It is returned when a caller opts
 // into denying public destinations via [WithDenyPublicIPs]; typical use
@@ -78,6 +85,18 @@ var nonPublicIPv6Prefixes = []netip.Prefix{
 	netip.MustParsePrefix("100::/64"),
 }
 
+// nonPublicIPv4Prefixes lists IPv4 ranges that the [netip.Addr] helpers do
+// not classify but that must not be considered public:
+//
+//   - 100.64.0.0/10 Carrier-grade NAT (RFC 6598). Routable inside provider
+//     and cluster networks, and Alibaba Cloud serves instance metadata from
+//     100.100.100.200.
+//   - 198.18.0.0/15 Benchmarking (RFC 2544). Never routed on the internet.
+var nonPublicIPv4Prefixes = []netip.Prefix{
+	netip.MustParsePrefix("100.64.0.0/10"),
+	netip.MustParsePrefix("198.18.0.0/15"),
+}
+
 // IsPublicIP reports whether addr is reachable on the public internet. It
 // returns false for loopback, private (RFC1918), link-local, unspecified,
 // multicast, and unique-local addresses. IPv4-mapped IPv6 addresses are
@@ -88,12 +107,20 @@ var nonPublicIPv6Prefixes = []netip.Prefix{
 // (6to4, Teredo, NAT64) are rejected wholesale rather than recursed into,
 // because a host that routes them implicitly trusts the IPv4 mapping and
 // the prefixes themselves are deprecated or translation-only. See
-// [nonPublicIPv6Prefixes] for the full list and rationale.
+// [nonPublicIPv6Prefixes] and [nonPublicIPv4Prefixes] for the full lists
+// and rationale.
+//
+// An IPv6 zone identifier is ignored, so [::%1] classifies the same as [::].
 func IsPublicIP(addr netip.Addr) bool {
 	if !addr.IsValid() {
 		return false
 	}
-	addr = addr.Unmap()
+	// A zone does not change where a non-link-local address routes, but
+	// [netip.Prefix.Contains] never matches a zoned address and
+	// [netip.Addr.IsUnspecified] compares the zone too. Keeping it would let
+	// http://[::%251]/ or any zoned address in the prefixes below pass as
+	// public.
+	addr = addr.WithZone("").Unmap()
 	switch {
 	case addr.IsLoopback(),
 		addr.IsPrivate(),
@@ -104,6 +131,13 @@ func IsPublicIP(addr netip.Addr) bool {
 		addr.IsInterfaceLocalMulticast():
 		return false
 	}
+	if addr.Is4() {
+		for _, p := range nonPublicIPv4Prefixes {
+			if p.Contains(addr) {
+				return false
+			}
+		}
+	}
 	if addr.Is6() {
 		for _, p := range nonPublicIPv6Prefixes {
 			if p.Contains(addr) {
@@ -249,7 +283,9 @@ func httpLikeScheme(scheme string) bool {
 //
 // The semantics:
 //
-//  1. The URL is parsed and its scheme and host lowercased.
+//  1. The URL is parsed, its scheme and host lowercased, and any userinfo
+//     dropped from the form the regexes see. The request still carries the
+//     credentials.
 //  2. allowList and denyList apply against the normalized form with OR
 //     semantics. The deny-list always applies.
 //  3. For http, https, ws, and wss, the host is resolved and every
@@ -268,26 +304,48 @@ func DecideOutbound(ctx context.Context, rawURL string, allowList, denyList []*r
 		opt(&cfg)
 	}
 
+	// Each match is bounded by [PatternMatchTimeout] rather than by the
+	// remaining budget, so an already-spent deadline no longer surfaces from
+	// the match itself. Schemes that resolve a host still learn about it from
+	// resolveHost, but a non-matching file:// or data: URL returns before that
+	// point, so check it here to keep failing closed on every path.
+	if !time.Now().Before(deadline) {
+		return OutboundDecision{}, context.DeadlineExceeded
+	}
+
 	parsed, err := url.Parse(rawURL)
 	if err != nil {
 		return OutboundDecision{}, fmt.Errorf("parse URL %q: %w", rawURL, ErrFiltered)
 	}
 	parsed.Scheme = strings.ToLower(parsed.Scheme)
 	parsed.Host = strings.ToLower(parsed.Host)
-	normalized := parsed.String()
+
+	// Match on a credential-free form. [url.URL.String] re-emits userinfo
+	// between "scheme://" and the host, so keeping it would let any
+	// "^https?://<host>" pattern be shifted past its own anchor:
+	// http://a@127.0.0.1/ escapes a deny-list anchored on 127\. and
+	// http://trusted.example.com@10.0.0.1/ satisfies an allow-list anchored on
+	// trusted\.example\.com. The host checks below already read
+	// [url.URL.Hostname], which ignores userinfo, so only the regex layer was
+	// affected. Dropping the credentials here also keeps them out of the error
+	// strings below, which reach operator logs and any OTEL log exporter.
+	matchable := *parsed
+	matchable.User = nil
+	normalized := matchable.String()
 
 	allowMatched := false
 	if len(allowList) > 0 {
 		for _, pattern := range allowList {
-			clone := regexp2.MustCompile(pattern.String(), 0)
-			clone.MatchTimeout = time.Until(deadline)
-
-			ok, err := clone.MatchString(normalized)
+			ok, err := MatchPattern(pattern, normalized)
 			if err != nil {
 				if time.Now().After(deadline) {
 					return OutboundDecision{}, context.DeadlineExceeded
 				}
-				return OutboundDecision{}, fmt.Errorf("'%s' cannot handle '%s': %w", clone.String(), normalized, err)
+				// The pattern could not be evaluated, so the URL cannot be
+				// cleared for the IP-check bypass an allow-list match grants.
+				// Fail closed like an unresolvable host does below, so the
+				// client gets a generic 403 rather than a 500.
+				return OutboundDecision{}, fmt.Errorf("'%s' cannot handle '%s': %v: %w", pattern.String(), normalized, err, ErrFiltered)
 			}
 
 			if ok {
@@ -302,15 +360,15 @@ func DecideOutbound(ctx context.Context, rawURL string, allowList, denyList []*r
 	}
 
 	for _, pattern := range denyList {
-		clone := regexp2.MustCompile(pattern.String(), 0)
-		clone.MatchTimeout = time.Until(deadline)
-
-		ok, err := clone.MatchString(normalized)
+		ok, err := MatchPattern(pattern, normalized)
 		if err != nil {
 			if time.Now().After(deadline) {
 				return OutboundDecision{}, context.DeadlineExceeded
 			}
-			return OutboundDecision{}, fmt.Errorf("'%s' cannot handle '%s': %w", clone.String(), normalized, err)
+			// The pattern could not be evaluated, so the URL cannot be proven
+			// to fall outside the deny-list. Fail closed rather than letting a
+			// deny-list that never ran pass the request through.
+			return OutboundDecision{}, fmt.Errorf("'%s' cannot handle '%s': %v: %w", pattern.String(), normalized, err, ErrFiltered)
 		}
 
 		if ok {
@@ -357,9 +415,8 @@ func DecideOutbound(ctx context.Context, rawURL string, allowList, denyList []*r
 }
 
 // FilterOutboundURL validates that rawURL is acceptable for an outbound
-// request from Gotenberg. It is the URL-aware replacement for
-// [FilterDeadline] and should be preferred for any new code that filters
-// a URL before issuing or instructing an outbound request.
+// request from Gotenberg. Prefer it for any new code that filters a URL
+// before issuing or instructing an outbound request.
 //
 // The default behavior is permissive: the URL passes as long as it clears
 // the regex allow-list and deny-list. Callers that need IP-class checks
@@ -436,6 +493,16 @@ func (rt *outboundRoundTripper) RoundTrip(req *http.Request) (*http.Response, er
 // gate this behind their module's opt-in flag. See
 // https://github.com/gotenberg/gotenberg/issues/1592.
 func NewOutboundHttpClient(timeout time.Duration, allowList, denyList []*regexp2.Regexp, enableEnvironmentProxy bool, opts ...DecideOption) *http.Client {
+	// A negative timeout means the caller's budget is already spent, which
+	// happens when it derives one from a deadline that has passed. [http.Client]
+	// treats any non-positive Timeout as no deadline at all, so passing it
+	// through would silently produce an unbounded client. Fail closed instead.
+	// Zero keeps meaning unbounded: callers that own the connection lifetime
+	// themselves pass it deliberately.
+	if timeout < 0 {
+		timeout = time.Nanosecond
+	}
+
 	base := http.DefaultTransport.(*http.Transport).Clone()
 
 	var proxyFunc func(*url.URL) (*url.URL, error)
@@ -479,6 +546,25 @@ func NewOutboundHttpClient(timeout time.Duration, allowList, denyList []*regexp2
 	}
 }
 
+// ClampedBackoff is a [retryablehttp.Backoff] that honors max on every path.
+//
+// [retryablehttp.DefaultBackoff] returns a Retry-After header from the remote
+// verbatim for 429 and 503, and returns it before applying its own max clamp.
+// A hostile origin therefore decides how long Gotenberg waits, and the wait is
+// not interruptible. Retry-After is still respected here, just never beyond
+// the ceiling the caller set.
+func ClampedBackoff(min, max time.Duration, attemptNum int, resp *http.Response) time.Duration {
+	wait := retryablehttp.DefaultBackoff(min, max, attemptNum, resp)
+	if wait > max {
+		return max
+	}
+	if wait < 0 {
+		return 0
+	}
+
+	return wait
+}
+
 // environmentProxyVariables are the variables golang.org/x/net/http/httpproxy
 // reads, in the casing precedence it applies.
 var environmentProxyVariables = []string{

pkg/gotenberg/outbound_test.go

@@ -3,11 +3,13 @@ package gotenberg
 import (
 	"context"
 	"errors"
+	"net/http"
 	"net/netip"
+	"strings"
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 )
 
 func TestIsPublicIP(t *testing.T) {
@@ -38,6 +40,24 @@ func TestIsPublicIP(t *testing.T) {
 
 		// Link-local.
 		{"169.254.169.254", false},
+		{"169.254.170.2", false},
+
+		// Carrier-grade NAT (RFC 6598). Alibaba Cloud serves instance
+		// metadata from 100.100.100.200.
+		{"100.64.0.0", false},
+		{"100.100.100.200", false},
+		{"100.127.255.255", false},
+		{"::ffff:100.100.100.200", false},
+
+		// Benchmarking (RFC 2544).
+		{"198.18.0.1", false},
+		{"198.19.255.255", false},
+
+		// Adjacent to the ranges above, and public.
+		{"100.63.255.255", true},
+		{"100.128.0.0", true},
+		{"198.17.255.255", true},
+		{"198.20.0.0", true},
 		{"fe80::1", false},
 
 		// Unique-local.
@@ -83,6 +103,23 @@ func TestIsPublicIP(t *testing.T) {
 
 		// Discard prefix (RFC 6666).
 		{"100::1", false},
+
+		// A zone identifier must not change the classification.
+		{"::%1", false},
+		{"::%lo", false},
+		{"::1%1", false},
+		{"fe80::1%eth0", false},
+		{"fc00::1%1", false},
+		{"::ffff:127.0.0.1%1", false},
+		{"fec0::1%eth0", false},
+		{"2002:a9fe:a9fe::%1", false},
+		{"2001:0:abcd:ef12:3456:7890:a9fe:a9fe%1", false},
+		{"64:ff9b::a9fe:a9fe%1", false},
+		{"64:ff9b:1::a9fe:a9fe%1", false},
+		{"::a9fe:a9fe%1", false},
+		{"2001:db8::1%1", false},
+		{"100::1%1", false},
+		{"2606:4700:4700::1111%1", true},
 	} {
 		t.Run(tc.addr, func(t *testing.T) {
 			addr, err := netip.ParseAddr(tc.addr)
@@ -127,10 +164,10 @@ func mustAddrs(t *testing.T, ss ...string) []netip.Addr {
 
 func TestFilterOutboundURL(t *testing.T) {
 	defaultDeny := []*regexp2.Regexp{
-		regexp2.MustCompile(`^https?://(10\.|172\.(1[6-9]|2[0-9]|3[01])\.|192\.168\.|169\.254\.|0\.0\.0\.0|127\.|localhost|\[::1\]|\[fd)`, 0),
+		regexp2.MustCompile(`^https?://(10\.|172\.(1[6-9]|2[0-9]|3[01])\.|192\.168\.|169\.254\.|0\.0\.0\.0|127\.|localhost|\[::1\]|\[fd)`, regexp2.None),
 	}
 	chromiumDeny := []*regexp2.Regexp{
-		regexp2.MustCompile(`^file:(?!//\/tmp/).*`, 0),
+		regexp2.MustCompile(`^file:(?!//\/tmp/).*`, regexp2.None),
 	}
 
 	for _, tc := range []struct {
@@ -209,7 +246,7 @@ func TestFilterOutboundURL(t *testing.T) {
 		{
 			scenario:  "allow-list match bypasses IP check",
 			rawURL:    "http://internal.service/api",
-			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^http://internal\.service`, 0)},
+			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^http://internal\.service`, regexp2.None)},
 			deny:      defaultDeny,
 			opts:      []DecideOption{WithDenyPrivateIPs(true)},
 			expectErr: false,
@@ -217,15 +254,15 @@ func TestFilterOutboundURL(t *testing.T) {
 		{
 			scenario:  "deny-list still wins over allow-list match",
 			rawURL:    "http://internal.service/api",
-			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^http://internal`, 0)},
-			deny:      []*regexp2.Regexp{regexp2.MustCompile(`/api$`, 0)},
+			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^http://internal`, regexp2.None)},
+			deny:      []*regexp2.Regexp{regexp2.MustCompile(`/api$`, regexp2.None)},
 			expectErr: true,
 			expectIs:  ErrFiltered,
 		},
 		{
 			scenario:  "allow-list non-empty and no match rejects",
 			rawURL:    "https://other.example/",
-			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^https://allowed\.example`, 0)},
+			allow:     []*regexp2.Regexp{regexp2.MustCompile(`^https://allowed\.example`, regexp2.None)},
 			expectErr: true,
 			expectIs:  ErrFiltered,
 		},
@@ -284,6 +321,22 @@ func TestFilterOutboundURL(t *testing.T) {
 			expectErr: true,
 			expectIs:  ErrFiltered,
 		},
+		{
+			scenario:  "zoned unspecified address blocked with deny-private-ips",
+			rawURL:    "http://[::%251]:9999/",
+			deny:      defaultDeny,
+			opts:      []DecideOption{WithDenyPrivateIPs(true)},
+			expectErr: true,
+			expectIs:  ErrFiltered,
+		},
+		{
+			scenario:  "zoned site-local address blocked with deny-private-ips",
+			rawURL:    "http://[fec0:1234::3%25eth0]:8080/",
+			deny:      defaultDeny,
+			opts:      []DecideOption{WithDenyPrivateIPs(true)},
+			expectErr: true,
+			expectIs:  ErrFiltered,
+		},
 	} {
 		t.Run(tc.scenario, func(t *testing.T) {
 			if tc.stub != nil {
@@ -486,7 +539,7 @@ func TestDecideOutbound_DenyLists_WinOverDenyPrivateIPs(t *testing.T) {
 	// The regex deny-list fires before any resolution; verifies that
 	// operator-supplied deny patterns remain effective regardless of
 	// IP-class options.
-	deny := []*regexp2.Regexp{regexp2.MustCompile(`^http://evil\.`, 0)}
+	deny := []*regexp2.Regexp{regexp2.MustCompile(`^http://evil\.`, regexp2.None)}
 
 	_, err := DecideOutbound(
 		context.Background(),
@@ -520,3 +573,236 @@ func TestDecideOutbound_Permissive_AllowsPrivate(t *testing.T) {
 		t.Fatalf("decision.Pinned = %v, want [10.0.0.5]", decision.Pinned)
 	}
 }
+
+// privateIPsDenyList is the textual private-IP deny-list that shipped as the
+// default for api-download-from-deny-list and webhook-deny-list in v8.31.0 and
+// is still published as a migration recipe. Every alternative is anchored on
+// "://", so userinfo used to slide the private address past the anchor.
+const privateIPsDenyList = `^https?://(10\.|172\.(1[6-9]|2[0-9]|3[01])\.|192\.168\.|169\.254\.|0\.0\.0\.0|127\.|localhost|\[::1\]|\[fd)`
+
+func TestDecideOutbound_UserinfoDoesNotEvadeDenyList(t *testing.T) {
+	for _, rawURL := range []string{
+		"http://127.0.0.1:9999/",
+		"http://a@127.0.0.1:9999/",
+		"http://@127.0.0.1:9999/",
+		"http://:@127.0.0.1:9999/",
+		"http://%61@127.0.0.1:9999/",
+		"http://user:pass@127.0.0.1:9999/",
+		"HTTP://A@127.0.0.1:9999/",
+		"http://a@169.254.169.254/latest/meta-data/",
+		// url.Parse takes the last "@" as the userinfo separator, so the host
+		// here is the second literal.
+		"http://a@127.0.0.1:9999@127.0.0.1:9999/",
+	} {
+		t.Run(rawURL, func(t *testing.T) {
+			withStubResolver(t, func(host string) ([]netip.Addr, error) {
+				t.Fatalf("unexpected DNS lookup for %q: the deny-list must reject before resolution", host)
+				return nil, nil
+			})
+
+			// Deny-list only, with the permissive IP defaults the modules ship.
+			_, err := DecideOutbound(
+				context.Background(),
+				rawURL,
+				nil,
+				[]*regexp2.Regexp{regexp2.MustCompile(privateIPsDenyList, regexp2.None)},
+				time.Now().Add(5*time.Second),
+			)
+			if !errors.Is(err, ErrFiltered) {
+				t.Fatalf("userinfo must not evade the deny-list, got: %v", err)
+			}
+		})
+	}
+}
+
+func TestDecideOutbound_UserinfoDoesNotSatisfyAllowList(t *testing.T) {
+	// A host-terminated allow-list, the shape the documentation recommends.
+	allowList := []*regexp2.Regexp{regexp2.MustCompile(`^https://trusted\.example\.com(:[0-9]+)?(/|$)`, regexp2.None)}
+
+	for _, rawURL := range []string{
+		"https://trusted.example.com@169.254.169.254/latest/meta-data/",
+		"https://trusted.example.com@10.0.0.5/",
+		"https://trusted.example.com:443@10.0.0.5/",
+	} {
+		t.Run(rawURL, func(t *testing.T) {
+			withStubResolver(t, func(host string) ([]netip.Addr, error) {
+				return mustAddrs(t, "10.0.0.5"), nil
+			})
+
+			decision, err := DecideOutbound(
+				context.Background(),
+				rawURL,
+				allowList, nil,
+				time.Now().Add(5*time.Second),
+				WithDenyPrivateIPs(true),
+			)
+			if err == nil {
+				t.Fatalf("userinfo must not satisfy the allow-list, got decision %+v", decision)
+			}
+			if decision.Bypass {
+				t.Fatal("userinfo must never produce a bypass")
+			}
+		})
+	}
+}
+
+func TestDecideOutbound_UserinfoKeptOutOfErrorMessages(t *testing.T) {
+	withStubResolver(t, func(host string) ([]netip.Addr, error) {
+		t.Fatalf("unexpected DNS lookup for %q", host)
+		return nil, nil
+	})
+
+	_, err := DecideOutbound(
+		context.Background(),
+		"http://alice:hunter2@127.0.0.1:9999/",
+		nil,
+		[]*regexp2.Regexp{regexp2.MustCompile(privateIPsDenyList, regexp2.None)},
+		time.Now().Add(5*time.Second),
+	)
+	if err == nil {
+		t.Fatal("expected the URL to be filtered")
+	}
+	if strings.Contains(err.Error(), "hunter2") || strings.Contains(err.Error(), "alice") {
+		t.Fatalf("error message must not leak URL credentials: %v", err)
+	}
+}
+
+func TestDecideOutbound_LegitimateCredentialsStillReachTheHost(t *testing.T) {
+	withStubResolver(t, func(host string) ([]netip.Addr, error) {
+		if host != "example.com" {
+			t.Fatalf("host = %q, want example.com: userinfo must not reach resolution", host)
+		}
+		return mustAddrs(t, "93.184.216.34"), nil
+	})
+
+	// Stripping userinfo is a matching concern only. A credentialed URL that
+	// breaks no rule must still be allowed through.
+	decision, err := DecideOutbound(
+		context.Background(),
+		"https://alice:hunter2@example.com/report.pdf",
+		[]*regexp2.Regexp{regexp2.MustCompile(`^https://example\.com(:[0-9]+)?(/|$)`, regexp2.None)},
+		nil,
+		time.Now().Add(5*time.Second),
+		WithDenyPrivateIPs(true),
+	)
+	if err != nil {
+		t.Fatalf("credentialed URL matching the allow-list must pass, got: %v", err)
+	}
+	if !decision.Bypass {
+		t.Fatalf("decision.Bypass = false, want true")
+	}
+}
+
+func TestClampedBackoff(t *testing.T) {
+	const (
+		min = 1 * time.Second
+		max = 30 * time.Second
+	)
+
+	retryAfter := func(status int, seconds string) *http.Response {
+		return &http.Response{StatusCode: status, Header: http.Header{"Retry-After": []string{seconds}}}
+	}
+
+	for _, tc := range []struct {
+		scenario string
+		resp     *http.Response
+		want     time.Duration
+	}{
+		{"429 with an hour is clamped", retryAfter(http.StatusTooManyRequests, "3600"), max},
+		{"429 with a day is clamped", retryAfter(http.StatusTooManyRequests, "86400"), max},
+		{"503 with an hour is clamped", retryAfter(http.StatusServiceUnavailable, "3600"), max},
+		{"429 under the ceiling is honored", retryAfter(http.StatusTooManyRequests, "5"), 5 * time.Second},
+		{"no response falls back to exponential", nil, min},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			got := ClampedBackoff(min, max, 0, tc.resp)
+			if got != tc.want {
+				t.Fatalf("ClampedBackoff = %s, want %s", got, tc.want)
+			}
+			if got > max {
+				t.Fatalf("ClampedBackoff = %s, which exceeds max %s", got, max)
+			}
+		})
+	}
+}
+
+// A negative max means the caller's budget is spent. The backoff must not
+// return a negative duration, which would make the retry loop spin.
+func TestClampedBackoff_NegativeMaxIsNotNegative(t *testing.T) {
+	got := ClampedBackoff(1*time.Second, -5*time.Second, 0, nil)
+	if got < 0 {
+		t.Fatalf("ClampedBackoff = %s, want a non-negative duration", got)
+	}
+}
+
+func TestNewOutboundHttpClient_NonPositiveTimeout(t *testing.T) {
+	// Zero stays unbounded: the LibreOffice proxy owns its own lifetime and
+	// passes it deliberately.
+	if got := NewOutboundHttpClient(0, nil, nil, false).Timeout; got != 0 {
+		t.Fatalf("timeout for 0 = %s, want 0", got)
+	}
+
+	// Negative means an expired budget. http.Client reads any non-positive
+	// Timeout as no deadline at all, so it must not be passed through.
+	if got := NewOutboundHttpClient(-5*time.Second, nil, nil, false).Timeout; got <= 0 {
+		t.Fatalf("timeout for a negative budget = %s, want a positive value so the client fails closed", got)
+	}
+}
+
+func TestDecideOutboundExpiredDeadline(t *testing.T) {
+	// Patterns are matched under the fixed PatternMatchTimeout rather than
+	// under the caller's remaining budget, so an expired deadline no longer
+	// surfaces from the match itself. Every scheme must still fail closed,
+	// including the ones that return before a host is resolved.
+	expired := time.Now().Add(-time.Second)
+
+	for _, rawURL := range []string{
+		"https://example.com/",
+		"file:///tmp/foo.html",
+		"data:text/html,hello",
+	} {
+		_, err := DecideOutbound(context.Background(), rawURL, nil, nil, expired)
+		if !errors.Is(err, context.DeadlineExceeded) {
+			t.Fatalf("DecideOutbound(%q) with an expired deadline = %v, want context.DeadlineExceeded", rawURL, err)
+		}
+	}
+}
+
+func TestDecideOutboundBoundsCatastrophicPatterns(t *testing.T) {
+	// A deny-list pattern that backtracks catastrophically, matched against a
+	// client-controlled URL. Before PatternMatchTimeout the ceiling was the
+	// caller's whole budget, so a 30s API_TIMEOUT bought a 30s CPU burn.
+	// The trailing "!" makes the match fail only after the nested quantifier
+	// has explored every way to split the run of "a"s.
+	pattern := regexp2.MustCompile(`^https://example\.com/(a+)+$`, regexp2.None)
+	pattern.MatchTimeout = PatternMatchTimeout
+
+	rawURL := "https://example.com/" + strings.Repeat("a", 40) + "!"
+
+	start := time.Now()
+	_, err := DecideOutbound(
+		context.Background(),
+		rawURL,
+		nil,
+		[]*regexp2.Regexp{pattern},
+		time.Now().Add(30*time.Second),
+	)
+	elapsed := time.Since(start)
+
+	if err == nil {
+		t.Fatal("expected an error from a catastrophic deny-list pattern")
+	}
+
+	// A deny-list that could not be evaluated cannot clear the URL, so the
+	// decision fails closed and the client gets a generic 403 rather than a
+	// 500 naming the pattern.
+	if !errors.Is(err, ErrFiltered) {
+		t.Fatalf("expected ErrFiltered from an unevaluable deny-list pattern but got: %v", err)
+	}
+
+	// Generous headroom over the 250ms ceiling, still far below the 30s
+	// deadline the match would otherwise have been allowed to consume.
+	if elapsed > 5*time.Second {
+		t.Fatalf("match took %s, want it aborted near PatternMatchTimeout (%s)", elapsed, PatternMatchTimeout)
+	}
+}

pkg/gotenberg/pattern.go

@@ -0,0 +1,55 @@
+package gotenberg
+
+import (
+	"github.com/dlclark/regexp2/v2"
+)
+
+// patternMatchAttempts caps how many times [MatchPattern] runs one pattern
+// against one string. It is what keeps a pattern that is genuinely out of
+// budget from retrying forever: three attempts bound its cost at three
+// [PatternMatchTimeout], which is still two orders of magnitude below the
+// --api-timeout (env API_TIMEOUT) the ceiling exists to protect.
+const patternMatchAttempts = 3
+
+// MatchPattern reports whether s matches pattern. It bounds the match by the
+// pattern's MatchTimeout without the false timeouts that the bound alone
+// produces.
+//
+// regexp2 does not time a match against [time.Now]. It derives the deadline
+// from a process-global clock that a background goroutine advances every
+// 100ms, and it tests that deadline on the very first step of the match.
+// Anything that stops the whole process, a cgroup CPU-quota throttle or a long
+// stop-the-world pause, also stops that goroutine, which then advances the
+// clock by the full pause in a single write. A match holding a deadline from
+// before that jump aborts whatever work it had done: a 366ns match against a
+// short URL reports "match timeout after 250ms". The abort lands on whichever
+// match straddles the jump rather than on a match that was slow, which is why
+// it fires on an idle instance and against Gotenberg's own file:///tmp/ URLs.
+// See https://github.com/gotenberg/gotenberg/issues/1659.
+//
+// Retrying separates the two cases. Catastrophic backtracking is
+// deterministic: the same pattern against the same string exhausts the same
+// budget on every attempt, so a genuine runaway still aborts, and costs at
+// most patternMatchAttempts ceilings to prove it. A clock-induced abort needs
+// the process to lose the CPU inside one specific match, which the next
+// attempt does not reproduce.
+//
+// Elapsed time cannot make that call instead. A match frozen mid-flight
+// reports the freeze as its own cost, 806ms against a 250ms ceiling in one
+// measured run, so it is indistinguishable by wall clock from a match that
+// really did spend its budget. Go exposes no per-goroutine CPU time, and
+// process CPU time counts every other request in flight.
+func MatchPattern(pattern *regexp2.Regexp, s string) (bool, error) {
+	var err error
+
+	for range patternMatchAttempts {
+		var ok bool
+
+		ok, err = pattern.MatchString(s)
+		if err == nil {
+			return ok, nil
+		}
+	}
+
+	return false, err
+}

pkg/gotenberg/pattern_test.go

@@ -0,0 +1,99 @@
+package gotenberg
+
+import (
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/dlclark/regexp2/v2"
+)
+
+// mustPattern compiles a pattern the way the production lists are built.
+func mustPattern(t *testing.T, expr string) *regexp2.Regexp {
+	t.Helper()
+
+	re := regexp2.MustCompile(expr, regexp2.None)
+	re.MatchTimeout = PatternMatchTimeout
+
+	return re
+}
+
+func TestMatchPattern(t *testing.T) {
+	// The abort [MatchPattern] absorbs cannot be staged here: it needs the
+	// whole process to lose the CPU around one specific match, which no test
+	// can schedule. What is testable is the other half of the contract, that
+	// retrying never turns a genuine runaway into a pass.
+	// See https://github.com/gotenberg/gotenberg/issues/1659.
+	for _, tc := range []struct {
+		scenario    string
+		pattern     *regexp2.Regexp
+		s           string
+		expectMatch bool
+		expectError bool
+	}{
+		{
+			scenario:    "deny-list match",
+			pattern:     mustPattern(t, `^file:(?!//\/tmp/).*`),
+			s:           "file:///etc/passwd",
+			expectMatch: true,
+		},
+		{
+			scenario:    "no match against Gotenberg's own working directory",
+			pattern:     mustPattern(t, `^file:(?!//\/tmp/).*`),
+			s:           "file:///tmp/1a2b3c4d/5e6f7a8b/9c0d1e2f.html",
+			expectMatch: false,
+		},
+		{
+			scenario:    "no match",
+			pattern:     mustPattern(t, `^https://example\.com/`),
+			s:           "https://example.org/",
+			expectMatch: false,
+		},
+		{
+			scenario:    "catastrophic backtracking still aborts",
+			pattern:     mustPattern(t, `^https://example\.com/(a+)+$`),
+			s:           "https://example.com/" + strings.Repeat("a", 40) + "!",
+			expectError: true,
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			ok, err := MatchPattern(tc.pattern, tc.s)
+
+			if tc.expectError && err == nil {
+				t.Fatal("expected an error but got none")
+			}
+
+			if !tc.expectError && err != nil {
+				t.Fatalf("expected no error but got: %v", err)
+			}
+
+			if ok != tc.expectMatch {
+				t.Fatalf("expected match %t but got %t", tc.expectMatch, ok)
+			}
+		})
+	}
+}
+
+func TestMatchPatternBoundsCatastrophicPattern(t *testing.T) {
+	// Proving a runaway is genuine costs one ceiling per attempt, so the
+	// worst case is patternMatchAttempts of them plus regexp2's clock period
+	// on each, roughly a second. The bound that matters is the one this
+	// replaced: before the ceiling existed, the same match was allowed to
+	// burn a core for the caller's whole 30s budget.
+	pattern := mustPattern(t, `^https://example\.com/(a+)+$`)
+	s := "https://example.com/" + strings.Repeat("a", 40) + "!"
+
+	start := time.Now()
+	_, err := MatchPattern(pattern, s)
+	elapsed := time.Since(start)
+
+	if err == nil {
+		t.Fatal("expected an error from a catastrophic pattern")
+	}
+
+	// Generous headroom over the expected second keeps this stable on a
+	// loaded CI box while still failing if the bound is gone.
+	if elapsed > 5*time.Second {
+		t.Fatalf("match took %s, want at most %d ceilings of %s", elapsed, patternMatchAttempts, PatternMatchTimeout)
+	}
+}

pkg/gotenberg/semconv/httpconvtest_test.go

@@ -201,17 +201,13 @@ func TestNewServerRecordMetrics(t *testing.T) {
 			server.RecordMetrics(t.Context(), semconv.ServerMetricData{
 				ServerName:   "stuff",
 				ResponseSize: 200,
-				MetricAttributes: semconv.MetricAttributes{
-					Req:        req,
-					StatusCode: 301,
-					AdditionalAttributes: []attribute.KeyValue{
-						attribute.String("key", "value"),
-					},
-				},
-				MetricData: semconv.MetricData{
-					RequestSize: 100,
-					ElapsedTime: 300,
+				Req:          req,
+				StatusCode:   301,
+				AdditionalAttributes: []attribute.KeyValue{
+					attribute.String("key", "value"),
 				},
+				RequestSize: 100,
+				ElapsedTime: 300,
 			})
 
 			rm := metricdata.ResourceMetrics{}

pkg/gotenberg/supervisor.go

@@ -59,8 +59,9 @@ type ProcessSupervisor interface {
 	// Healthy checks and returns the health status of the managed [Process].
 	//
 	// A non-started process is considered healthy (startup is deferred until
-	// the first request). Returns false if the process is currently restarting
-	// or is reported unhealthy by the underlying [Process].
+	// the first request), as is one going through a planned restart, since it
+	// keeps serving traffic. Returns false during an unplanned restart or when
+	// the underlying [Process] reports unhealthy.
 	Healthy() bool
 
 	// Run executes a provided task while managing the state of the [Process].
@@ -103,6 +104,28 @@ const healthCheckCacheTTL = 2 * time.Second
 // this. See https://github.com/gotenberg/gotenberg/issues/1561.
 const healthFailureThreshold = 2
 
+// Restart reasons, also reported as the gotenberg.process.start.reason span
+// attribute by [processSupervisor.tracedLaunch]. Only
+// [restartReasonMaxRequests] is a planned restart: it fires on a healthy
+// process that reached its conversion limit, so the node keeps serving
+// traffic throughout. The others signal a process that cannot serve.
+const (
+	restartReasonFirstStart  = "first_start"
+	restartReasonUnhealthy   = "unhealthy"
+	restartReasonMaxRequests = "max_requests"
+)
+
+// defaultEagerRestartTimeout bounds the restart triggered after the maximum
+// request limit. That restart runs on a background context, unlike the one from
+// ensureHealthy which inherits the request deadline, so without a deadline of
+// its own the drain loop in [processSupervisor.doRestartLocked] would wait
+// forever on a task that never completes. That would pin isRestarting and,
+// with it, the health reported by [processSupervisor.Healthy]. Sized well above
+// --api-timeout (30s by default) plus the engine start timeouts (20s by
+// default) so it never fires while tasks are merely slow. The eager restart is
+// opportunistic: on expiry it aborts, and the next task retries it.
+const defaultEagerRestartTimeout = 2 * time.Minute
+
 type processSupervisor struct {
 	logger         *slog.Logger
 	engine         string
@@ -118,11 +141,16 @@ type processSupervisor struct {
 	// transient failure (such as a cold-start timeout) must not poison the
 	// supervisor for the rest of the container's lifetime. See
 	// https://github.com/gotenberg/gotenberg/issues/1538.
-	firstStartMu        sync.Mutex
-	reqCounter          atomic.Int64
-	reqQueueSize        atomic.Int64
-	restartsCounter     atomic.Int64
-	isRestarting        atomic.Bool
+	firstStartMu    sync.Mutex
+	reqCounter      atomic.Int64
+	reqQueueSize    atomic.Int64
+	restartsCounter atomic.Int64
+	isRestarting    atomic.Bool
+	// restartPlanned records whether the in-flight restart is a planned one
+	// (see [restartReasonMaxRequests]). Written before isRestarting and never
+	// cleared, so a reader that observed isRestarting always sees the matching
+	// kind. See [processSupervisor.Healthy].
+	restartPlanned      atomic.Bool
 	activeTasks         atomic.Int64
 	restartMutex        sync.Mutex
 	idleShutdownTimeout time.Duration
@@ -135,6 +163,9 @@ type processSupervisor struct {
 	consecutiveHealthFailures atomic.Int64  // reset to 0 on every successful probe
 	idleMu                    sync.Mutex    // protects idleStopChan
 	idleStopChan              chan struct{} // signal to stop the idle ticker goroutine
+	// eagerRestartTimeout bounds the restart from maybeRestartAfterTask.
+	// Defaults to [defaultEagerRestartTimeout]; only tests shorten it.
+	eagerRestartTimeout time.Duration
 }
 
 // NewProcessSupervisor initializes a new [ProcessSupervisor]. engine names the
@@ -158,6 +189,7 @@ func NewProcessSupervisor(logger *slog.Logger, engine string, process Process, m
 		maxQueueSize:        maxQueueSize,
 		maxConcurrency:      maxConcurrency,
 		idleShutdownTimeout: idleShutdownTimeout,
+		eagerRestartTimeout: defaultEagerRestartTimeout,
 	}
 	b.reqCounter.Store(0)
 	b.reqQueueSize.Store(0)
@@ -212,12 +244,18 @@ func (s *processSupervisor) restart() error {
 		s.logger.WarnContext(context.Background(), fmt.Sprintf("stop process before restart: %s", err))
 	}
 
+	// Reset the counter on the attempt, not on its outcome. Leaving it at the
+	// limit after a failed launch re-triggers maybeRestartAfterTask on every
+	// subsequent task, producing back-to-back restarts. Recovering a process
+	// that will not start is ensureHealthy's job: it restarts synchronously
+	// before running a task, and reports the failure to the caller.
+	s.reqCounter.Store(0)
+
 	err = s.Launch()
 	if err != nil {
 		return fmt.Errorf("restart process: %w", err)
 	}
 
-	s.reqCounter.Store(0)
 	s.restartsCounter.Add(1)
 	s.logger.DebugContext(context.Background(), "process successfully restarted")
 
@@ -234,9 +272,17 @@ func (s *processSupervisor) Healthy() bool {
 	}
 
 	if s.isRestarting.Load() {
-		// A restarting process is not yet healthy. This gives load balancers
-		// honest information so they can avoid routing traffic to this node.
-		return false
+		// A planned restart is routine maintenance: the process reached the
+		// limit set by --chromium-restart-after (env CHROMIUM_RESTART_AFTER) or
+		// --libreoffice-restart-after (env LIBREOFFICE_RESTART_AFTER) while
+		// healthy. Tasks arriving during it are requeued by acquireSlot, not
+		// rejected, so the node still serves traffic and must report healthy. A
+		// probe sent between two conversions used to fail here.
+		// See https://github.com/gotenberg/gotenberg/issues/1648.
+		//
+		// An unplanned restart keeps reporting unhealthy, which gives load
+		// balancers honest information so they can avoid routing traffic here.
+		return s.restartPlanned.Load()
 	}
 
 	// Cache hit: a recent probe succeeded. Skip the CDP roundtrip so probe
@@ -484,7 +530,7 @@ func (s *processSupervisor) ensureStarted(ctx context.Context) error {
 		return nil
 	}
 
-	err := s.tracedLaunch(ctx, "first_start", func() error {
+	err := s.tracedLaunch(ctx, restartReasonFirstStart, func() error {
 		return s.runWithDeadline(ctx, s.Launch)
 	})
 	if err != nil {
@@ -525,7 +571,7 @@ func (s *processSupervisor) ensureHealthy(ctx context.Context) error {
 
 	s.logger.DebugContext(context.Background(), "process is unhealthy, cannot handle task, restarting...")
 
-	if err := s.doRestart(ctx, "unhealthy"); err != nil {
+	if err := s.doRestart(ctx, restartReasonUnhealthy); err != nil {
 		return fmt.Errorf("process restart before task: %w", err)
 	}
 
@@ -533,9 +579,10 @@ func (s *processSupervisor) ensureHealthy(ctx context.Context) error {
 }
 
 // maybeRestartAfterTask checks if the maximum request limit has been reached
-// and, if so, triggers an asynchronous restart. If a restart is initiated, it
-// takes ownership of the caller's semaphore slot (the caller must not release
-// it). Returns true if ownership was taken.
+// and, if so, triggers an asynchronous restart bounded by
+// [defaultEagerRestartTimeout]. If a restart is initiated, it takes ownership
+// of the caller's semaphore slot (the caller must not release it). Returns true
+// if ownership was taken.
 func (s *processSupervisor) maybeRestartAfterTask(logger *slog.Logger) bool {
 	if s.maxReqLimit <= 0 || s.reqCounter.Load() < s.maxReqLimit {
 		return false
@@ -548,7 +595,10 @@ func (s *processSupervisor) maybeRestartAfterTask(logger *slog.Logger) bool {
 	s.logger.DebugContext(context.Background(), "max request limit reached, restarting eagerly...")
 
 	go func() {
-		restartErr := s.doRestartLocked(context.Background(), "max_requests")
+		ctx, cancel := context.WithTimeout(context.Background(), s.eagerRestartTimeout)
+		defer cancel()
+
+		restartErr := s.doRestartLocked(ctx, restartReasonMaxRequests)
 		s.restartMutex.Unlock()
 		if restartErr != nil {
 			s.logger.ErrorContext(context.Background(), fmt.Sprintf("process restart after task: %v", restartErr))
@@ -571,6 +621,10 @@ func (s *processSupervisor) doRestart(ctx context.Context, reason string) error
 
 // doRestartLocked performs the restart drain logic. The caller must hold restartMutex.
 func (s *processSupervisor) doRestartLocked(ctx context.Context, reason string) error {
+	// Publish the kind before raising the flag. [processSupervisor.Healthy]
+	// reads restartPlanned only after it observes isRestarting, so this
+	// ordering keeps it from pairing a new restart with a stale kind.
+	s.restartPlanned.Store(reason == restartReasonMaxRequests)
 	s.isRestarting.Store(true)
 	defer s.isRestarting.Store(false)
 

pkg/gotenberg/supervisor_test.go

@@ -160,13 +160,49 @@ func TestProcessSupervisor_restart(t *testing.T) {
 	}
 }
 
+// TestProcessSupervisor_restart_ResetsCounterOnFailedLaunch verifies that a
+// restart whose launch fails still clears the request counter. Leaving it at
+// the limit makes maybeRestartAfterTask re-fire on every subsequent task.
+func TestProcessSupervisor_restart_ResetsCounterOnFailedLaunch(t *testing.T) {
+	logger := slog.New(slog.DiscardHandler)
+
+	const maxReqLimit = 5
+
+	process := &ProcessMock{
+		StartMock:   func(_ *slog.Logger) error { return errors.New("start error") },
+		StopMock:    func(_ *slog.Logger) error { return nil },
+		HealthyMock: func(_ *slog.Logger) bool { return true },
+	}
+
+	ps := NewProcessSupervisor(logger, "test", process, maxReqLimit, 0, 1, 0).(*processSupervisor)
+	ps.reqCounter.Store(maxReqLimit)
+
+	err := ps.restart()
+	if err == nil {
+		t.Fatal("expected error but got none")
+	}
+
+	if got := ps.reqCounter.Load(); got != 0 {
+		t.Fatalf("expected the request counter to be reset but got %d", got)
+	}
+
+	if got := ps.restartsCounter.Load(); got != 0 {
+		t.Fatalf("expected the restarts counter to stay at 0 but got %d", got)
+	}
+
+	if ps.maybeRestartAfterTask(logger) {
+		t.Fatal("expected no further eager restart to be triggered")
+	}
+}
+
 func TestProcessSupervisor_Healthy(t *testing.T) {
 	for _, tc := range []struct {
-		scenario            string
-		initiallyStarted    bool
-		initiallyRestarting bool
-		processHealthy      bool
-		expectHealthy       bool
+		scenario                string
+		initiallyStarted        bool
+		initiallyRestarting     bool
+		initiallyRestartPlanned bool
+		processHealthy          bool
+		expectHealthy           bool
 	}{
 		{
 			scenario:         "non-started process is healthy",
@@ -179,6 +215,13 @@ func TestProcessSupervisor_Healthy(t *testing.T) {
 			initiallyRestarting: true,
 			expectHealthy:       false,
 		},
+		{
+			scenario:                "process going through a planned restart is healthy",
+			initiallyStarted:        true,
+			initiallyRestarting:     true,
+			initiallyRestartPlanned: true,
+			expectHealthy:           true,
+		},
 		{
 			scenario:         "process reports as healthy",
 			initiallyStarted: true,
@@ -208,6 +251,9 @@ func TestProcessSupervisor_Healthy(t *testing.T) {
 			if tc.initiallyRestarting {
 				ps.isRestarting.Store(true)
 			}
+			if tc.initiallyRestartPlanned {
+				ps.restartPlanned.Store(true)
+			}
 
 			healthy := ps.Healthy()
 
@@ -257,6 +303,204 @@ func TestProcessSupervisor_Healthy_ConsecutiveFailures(t *testing.T) {
 	}
 }
 
+// TestProcessSupervisor_Healthy_PlannedRestart reproduces
+// https://github.com/gotenberg/gotenberg/issues/1648. It drives the real
+// Run() path until the maximum request limit triggers the eager restart, then
+// asserts the supervisor reports healthy while that restart is in flight.
+// Tasks arriving during it are requeued by acquireSlot, not rejected, so the
+// node still serves traffic.
+func TestProcessSupervisor_Healthy_PlannedRestart(t *testing.T) {
+	logger := slog.New(slog.DiscardHandler)
+
+	const maxReqLimit = 10
+
+	restarting := make(chan struct{})
+	release := make(chan struct{})
+
+	var (
+		starts    atomic.Int64
+		signalOne sync.Once
+	)
+	process := &ProcessMock{
+		StartMock: func(_ *slog.Logger) error {
+			// Hold the restart open so the assertions below run inside the
+			// window that used to report unhealthy.
+			if starts.Add(1) > 1 {
+				signalOne.Do(func() { close(restarting) })
+				<-release
+			}
+
+			return nil
+		},
+		StopMock:    func(_ *slog.Logger) error { return nil },
+		HealthyMock: func(_ *slog.Logger) bool { return true },
+	}
+
+	ps := NewProcessSupervisor(logger, "test", process, maxReqLimit, 0, 1, 0).(*processSupervisor)
+
+	for i := range maxReqLimit {
+		err := ps.Run(context.Background(), logger, func() error { return nil })
+		if err != nil {
+			t.Fatalf("task %d: expected no error but got: %v", i+1, err)
+		}
+	}
+
+	select {
+	case <-restarting:
+	case <-time.After(10 * time.Second):
+		t.Fatalf("expected an eager restart after %d tasks", maxReqLimit)
+	}
+
+	if !ps.isRestarting.Load() {
+		t.Fatal("expected the supervisor to be restarting")
+	}
+
+	if !ps.restartPlanned.Load() {
+		t.Fatal("expected the restart to be flagged as planned")
+	}
+
+	if !ps.Healthy() {
+		t.Fatal("expected a planned restart to report healthy")
+	}
+
+	close(release)
+}
+
+// TestProcessSupervisor_Healthy_UnplannedRestart verifies the counterpart of
+// [TestProcessSupervisor_Healthy_PlannedRestart]: a restart triggered by an
+// unhealthy process keeps reporting unhealthy, so load balancers get honest
+// information.
+func TestProcessSupervisor_Healthy_UnplannedRestart(t *testing.T) {
+	logger := slog.New(slog.DiscardHandler)
+
+	restarting := make(chan struct{})
+	release := make(chan struct{})
+
+	var signalOne sync.Once
+	process := &ProcessMock{
+		StartMock: func(_ *slog.Logger) error {
+			signalOne.Do(func() { close(restarting) })
+			<-release
+
+			return nil
+		},
+		StopMock:    func(_ *slog.Logger) error { return nil },
+		HealthyMock: func(_ *slog.Logger) bool { return false },
+	}
+
+	ps := NewProcessSupervisor(logger, "test", process, 0, 0, 1, 0).(*processSupervisor)
+	ps.firstStart.Store(true)
+
+	go func() {
+		_ = ps.ensureHealthy(context.Background())
+	}()
+
+	select {
+	case <-restarting:
+	case <-time.After(10 * time.Second):
+		t.Fatal("expected an unhealthy restart to be triggered")
+	}
+
+	if !ps.isRestarting.Load() {
+		t.Fatal("expected the supervisor to be restarting")
+	}
+
+	if ps.restartPlanned.Load() {
+		t.Fatal("expected the restart not to be flagged as planned")
+	}
+
+	if ps.Healthy() {
+		t.Fatal("expected an unplanned restart to report unhealthy")
+	}
+
+	close(release)
+}
+
+// TestProcessSupervisor_doRestartLocked_DrainDeadline verifies that a drain
+// unable to acquire every slot gives up on the context deadline and clears
+// isRestarting. Without a deadline on the eager restart, a task that never
+// completes would pin the flag and, since a planned restart reports healthy,
+// leave the supervisor claiming health forever.
+func TestProcessSupervisor_doRestartLocked_DrainDeadline(t *testing.T) {
+	logger := slog.New(slog.DiscardHandler)
+
+	var starts atomic.Int64
+	process := &ProcessMock{
+		StartMock: func(_ *slog.Logger) error {
+			starts.Add(1)
+
+			return nil
+		},
+		StopMock:    func(_ *slog.Logger) error { return nil },
+		HealthyMock: func(_ *slog.Logger) bool { return true },
+	}
+
+	// A concurrency of 2 makes the drain acquire one slot on top of the one the
+	// triggering task hands over. Fill the semaphore so it never can, mimicking
+	// a concurrent task that never completes.
+	ps := NewProcessSupervisor(logger, "test", process, 1, 0, 2, 0).(*processSupervisor)
+	ps.semaphore <- struct{}{}
+	ps.semaphore <- struct{}{}
+
+	ctx, cancel := context.WithTimeout(context.Background(), 50*time.Millisecond)
+	defer cancel()
+
+	err := ps.doRestartLocked(ctx, restartReasonMaxRequests)
+	if err == nil {
+		t.Fatal("expected the drain to fail on the context deadline")
+	}
+
+	if ps.isRestarting.Load() {
+		t.Fatal("expected isRestarting to be cleared after a failed drain")
+	}
+
+	if starts.Load() != 0 {
+		t.Fatalf("expected no restart attempt after a failed drain but got %d", starts.Load())
+	}
+}
+
+// TestProcessSupervisor_maybeRestartAfterTask_Bounded verifies that the eager
+// restart runs under a deadline. A concurrent task that never completes blocks
+// the drain, and without a bound the restart goroutine would wait forever with
+// isRestarting pinned, leaving Healthy() reporting a planned restart for good.
+func TestProcessSupervisor_maybeRestartAfterTask_Bounded(t *testing.T) {
+	logger := slog.New(slog.DiscardHandler)
+
+	process := &ProcessMock{
+		StartMock:   func(_ *slog.Logger) error { return nil },
+		StopMock:    func(_ *slog.Logger) error { return nil },
+		HealthyMock: func(_ *slog.Logger) bool { return true },
+	}
+
+	ps := NewProcessSupervisor(logger, "test", process, 1, 0, 2, 0).(*processSupervisor)
+	ps.eagerRestartTimeout = 100 * time.Millisecond
+	ps.firstStart.Store(true)
+
+	// Wedge one slot so the drain, which needs one on top of the slot the
+	// triggering task hands over, can never complete.
+	ps.semaphore <- struct{}{}
+
+	err := ps.Run(context.Background(), logger, func() error { return nil })
+	if err != nil {
+		t.Fatalf("expected no error but got: %v", err)
+	}
+
+	waitFor := func(what string, want bool) {
+		t.Helper()
+
+		deadline := time.Now().Add(5 * time.Second)
+		for ps.isRestarting.Load() != want {
+			if time.Now().After(deadline) {
+				t.Fatalf("timed out waiting for the eager restart to %s", what)
+			}
+			time.Sleep(5 * time.Millisecond)
+		}
+	}
+
+	waitFor("start", true)
+	waitFor("give up on its deadline", false)
+}
+
 // TestProcessSupervisor_Healthy_CachesPositiveResult verifies that a
 // successful probe is cached for [healthCheckCacheTTL] so subsequent
 // supervisor.Healthy() calls do not re-issue the underlying process

pkg/modules/api/api.go

@@ -12,10 +12,9 @@ import (
 	"time"
 
 	"github.com/alexliesenfeld/health"
-	"github.com/dlclark/regexp2"
-	"github.com/labstack/echo/v4"
+	"github.com/dlclark/regexp2/v2"
+	"github.com/labstack/echo/v5"
 	flag "github.com/spf13/pflag"
-	"golang.org/x/net/http2"
 	"golang.org/x/sync/errgroup"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
@@ -58,6 +57,12 @@ type Api struct {
 	fs                  *gotenberg.FileSystem
 	logger              *slog.Logger
 	srv                 *echo.Echo
+
+	// shutdownCancel triggers the graceful shutdown of the server started by
+	// [echo.StartConfig]. Echo v5 drives shutdown from a context instead of an
+	// Echo.Shutdown method. serveDone closes once that shutdown completed.
+	shutdownCancel context.CancelFunc
+	serveDone      chan struct{}
 }
 
 type downloadFromConfig struct {
@@ -67,6 +72,8 @@ type downloadFromConfig struct {
 	denyPublicIPs          bool
 	enableEnvironmentProxy bool
 	maxRetry               int
+	maxConcurrency         int
+	maxEntries             int
 	disable                bool
 }
 
@@ -132,7 +139,7 @@ const (
 //	middleware := Middleware{
 //	  Handler: func() echo.MiddlewareFunc {
 //	    return func(next echo.HandlerFunc) echo.HandlerFunc {
-//	      return func(c echo.Context) error {
+//	      return func(c *echo.Context) error {
 //	        rootPath := c.Get("rootPath").(string)
 //	        healthURI := fmt.Sprintf("%shealth", rootPath)
 //
@@ -206,12 +213,14 @@ func (a *Api) Descriptor() gotenberg.ModuleDescriptor {
 			fs.String("api-oidc-issuer", "", "Set the OIDC issuer URL, e.g. https://tenant.example.com/ - the token 'iss' claim must match")
 			fs.String("api-oidc-audience", "", "Set the expected OIDC audience - the token 'aud' claim must contain it")
 			fs.String("api-oidc-jwks-url", "", "Set the OIDC JWKS URL - discovered from the issuer's well-known configuration when empty")
-			fs.StringSlice("api-download-from-allow-list", []string{}, "Set the allowed URLs for the download from feature using regular expressions - supports multiple values")
+			fs.StringSlice("api-download-from-allow-list", []string{}, `Set the allowed URLs for the download from feature using regular expressions - supports multiple values. A match bypasses --api-download-from-deny-private-ips (API_DOWNLOAD_FROM_DENY_PRIVATE_IPS) and --api-download-from-deny-public-ips (API_DOWNLOAD_FROM_DENY_PUBLIC_IPS), so terminate the host or the pattern also matches suffix hosts, for example ^https?://internal\.svc(:|/|$)`)
 			fs.StringSlice("api-download-from-deny-list", []string{}, "Set the denied URLs for the download from feature using regular expressions - supports multiple values")
 			fs.Bool("api-download-from-deny-private-ips", false, "Reject downloadFrom URLs whose host resolves to a non-public IP address (loopback, RFC1918, link-local, unique-local). Enable on deployments that accept untrusted downloadFrom sources to mitigate SSRF against internal services")
 			fs.Bool("api-download-from-deny-public-ips", false, "Reject downloadFrom URLs whose host resolves to a public IP address. Enable on air-gapped or data-governed deployments to prevent downloads from reaching the public internet")
 			fs.Bool("api-download-from-enable-environment-proxy", false, "Route downloadFrom fetches through the proxy defined by the standard HTTP_PROXY, HTTPS_PROXY, and NO_PROXY variables, including credentials")
 			fs.Int("api-download-from-max-retry", 4, "Set the maximum number of retries for the download from feature")
+			fs.Int("api-download-from-max-concurrency", 10, "Set the maximum number of downloadFrom entries fetched concurrently per request - bounds the outbound fan-out. Set to 0 to disable this feature")
+			fs.Int("api-download-from-max-entries", 0, "Set the maximum number of downloadFrom entries allowed per request. Set to 0 to disable this feature")
 			fs.Bool("api-disable-download-from", false, "Disable the download from feature")
 			fs.Bool("api-disable-health-check-route-telemetry", true, "Disable telemetry for health check route")
 			fs.Bool("api-disable-root-route-telemetry", true, "Disable telemetry for the root route")
@@ -255,6 +264,8 @@ func (a *Api) Provision(ctx *gotenberg.Context) error {
 		denyPublicIPs:          flags.MustBool("api-download-from-deny-public-ips"),
 		enableEnvironmentProxy: flags.MustBool("api-download-from-enable-environment-proxy"),
 		maxRetry:               flags.MustInt("api-download-from-max-retry"),
+		maxConcurrency:         flags.MustInt("api-download-from-max-concurrency"),
+		maxEntries:             flags.MustInt("api-download-from-max-entries"),
 		disable:                flags.MustBool("api-disable-download-from"),
 	}
 	a.disableHealthCheckRouteTelemetry = flags.MustDeprecatedBool("api-disable-health-check-logging", "api-disable-health-check-route-telemetry")
@@ -377,12 +388,37 @@ func (a *Api) Provision(ctx *gotenberg.Context) error {
 	// Logger.
 	a.logger = gotenberg.Logger(a)
 
+	a.warnInsecureDebugRoute()
+
 	// File system.
 	a.fs = gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
 
 	return nil
 }
 
+// warnInsecureDebugRoute logs a warning when the debug route is reachable
+// without authentication.
+//
+// The route reports the resolved configuration of every module, which is
+// useful to an operator and equally useful to anyone else who can reach it.
+// This warns rather than refuses: an operator may sit behind a gateway that
+// authenticates on Gotenberg's behalf, and failing startup would break them.
+func (a *Api) warnInsecureDebugRoute() {
+	if !a.enableDebugRoute || a.basicAuthUsername != "" || a.oidcEnabled {
+		return
+	}
+	if a.logger == nil {
+		return
+	}
+
+	a.logger.WarnContext(
+		context.Background(),
+		"--api-enable-debug-route (API_ENABLE_DEBUG_ROUTE) is enabled but no authentication is configured, so anyone who can reach Gotenberg can read its configuration. Set --api-enable-basic-auth (API_ENABLE_BASIC_AUTH) with GOTENBERG_API_BASIC_AUTH_USERNAME and GOTENBERG_API_BASIC_AUTH_PASSWORD, set --api-enable-oidc-auth (API_ENABLE_OIDC_AUTH), or disable the route.",
+		slog.String("flag", "--api-enable-debug-route"),
+		slog.String("env", "API_ENABLE_DEBUG_ROUTE"),
+	)
+}
+
 // Validate validates the module properties.
 func (a *Api) Validate() error {
 	var err error
@@ -404,6 +440,18 @@ func (a *Api) Validate() error {
 		}
 	}
 
+	if a.downloadFromCfg.maxConcurrency < 0 {
+		err = errors.Join(err,
+			fmt.Errorf("download from max concurrency must not be negative, got %d; set --api-download-from-max-concurrency (env API_DOWNLOAD_FROM_MAX_CONCURRENCY) to 0 to disable the limit", a.downloadFromCfg.maxConcurrency),
+		)
+	}
+
+	if a.downloadFromCfg.maxEntries < 0 {
+		err = errors.Join(err,
+			fmt.Errorf("download from max entries must not be negative, got %d; set --api-download-from-max-entries (env API_DOWNLOAD_FROM_MAX_ENTRIES) to 0 to disable the limit", a.downloadFromCfg.maxEntries),
+		)
+	}
+
 	if (a.tlsCertFile != "" && a.tlsKeyFile == "") || (a.tlsCertFile == "" && a.tlsKeyFile != "") {
 		err = errors.Join(err,
 			errors.New("both TLS certificate and key files must be set"),
@@ -493,16 +541,29 @@ func (a *Api) Validate() error {
 	return nil
 }
 
+// newEchoServer builds the [echo.Echo] instance with the settings Gotenberg
+// relies on, independently of the routes and middlewares added by [Api.Start].
+func newEchoServer() *echo.Echo {
+	srv := echo.New()
+	srv.HTTPErrorHandler = httpErrorHandler()
+	// Echo v5 serves files through Echo.Filesystem, an [fs.FS] rooted at the
+	// working directory, and [fs.FS] rejects absolute names. Every output file
+	// lives under the request's temporary directory, so Context.Attachment gets
+	// an absolute path and the default filesystem answers 404 for every
+	// conversion. Rooting at "/" restores the v4 behavior, where the path was
+	// opened as-is.
+	srv.Filesystem = echo.NewDefaultFS("/")
+	// Echo v5 dropped the X-Forwarded-For and X-Real-IP fallbacks from
+	// Context.RealIP. Keep the previous behavior so that the access log still
+	// reports the client IP when Gotenberg sits behind a reverse proxy.
+	srv.IPExtractor = echo.LegacyIPExtractor()
+
+	return srv
+}
+
 // Start starts the HTTP server.
 func (a *Api) Start() error {
-	a.srv = echo.New()
-	a.srv.HideBanner = true
-	a.srv.HidePort = true
-	a.srv.Server.ReadTimeout = a.timeout
-	a.srv.Server.IdleTimeout = a.timeout
-	// See https://github.com/gotenberg/gotenberg/issues/396.
-	a.srv.Server.WriteTimeout = a.timeout + a.timeout
-	a.srv.HTTPErrorHandler = httpErrorHandler()
+	a.srv = newEchoServer()
 
 	// Let's prepare the modules' routes.
 	var disableTelemetryForPaths []string
@@ -566,7 +627,7 @@ func (a *Api) Start() error {
 		securityMiddleware = oidcAuthMiddleware(verifier)
 	default:
 		securityMiddleware = func(next echo.HandlerFunc) echo.HandlerFunc {
-			return func(c echo.Context) error {
+			return func(c *echo.Context) error {
 				return next(c)
 			}
 		}
@@ -598,7 +659,7 @@ func (a *Api) Start() error {
 	// Root route.
 	a.srv.GET(
 		a.rootPath,
-		func(c echo.Context) error {
+		func(c *echo.Context) error {
 			return c.HTML(http.StatusOK, `Hey, Gotenberg has no UI, it's an API. Head to the <a href="https://gotenberg.dev">documentation</a> to learn how to interact with it 🚀`)
 		},
 		securityMiddleware,
@@ -607,7 +668,7 @@ func (a *Api) Start() error {
 	// Favicon route.
 	a.srv.GET(
 		fmt.Sprintf("%s%s", a.rootPath, "favicon.ico"),
-		func(c echo.Context) error {
+		func(c *echo.Context) error {
 			return c.NoContent(http.StatusNoContent)
 		},
 		securityMiddleware,
@@ -638,7 +699,7 @@ func (a *Api) Start() error {
 	// ...the version route.
 	a.srv.GET(
 		fmt.Sprintf("%s%s", a.rootPath, "version"),
-		func(c echo.Context) error {
+		func(c *echo.Context) error {
 			return c.String(http.StatusOK, gotenberg.Version)
 		},
 		securityMiddleware,
@@ -648,7 +709,7 @@ func (a *Api) Start() error {
 	if a.enableDebugRoute {
 		a.srv.GET(
 			fmt.Sprintf("%s%s", a.rootPath, "debug"),
-			func(c echo.Context) error {
+			func(c *echo.Context) error {
 				return c.JSONPretty(http.StatusOK, gotenberg.Debug(), "  ")
 			},
 			securityMiddleware,
@@ -669,18 +730,50 @@ func (a *Api) Start() error {
 		return fmt.Errorf("waiting for modules readiness: %w", err)
 	}
 
+	startConfig := echo.StartConfig{
+		Address:    fmt.Sprintf("%s:%d", a.bindIp, a.port),
+		HideBanner: true,
+		HidePort:   true,
+		BeforeServeFunc: func(s *http.Server) error {
+			s.ReadTimeout = a.timeout
+			s.IdleTimeout = a.timeout
+			// See https://github.com/gotenberg/gotenberg/issues/396.
+			s.WriteTimeout = a.timeout + a.timeout
+
+			if a.tlsCertFile == "" || a.tlsKeyFile == "" {
+				// Serve HTTP/2 Cleartext (h2c). Echo v5 dropped
+				// StartH2CServer and golang.org/x/net/http2/h2c is deprecated,
+				// so the standard library serves h2c through Server.Protocols
+				// instead.
+				protocols := new(http.Protocols)
+				protocols.SetHTTP1(true)
+				protocols.SetUnencryptedHTTP2(true)
+				s.Protocols = protocols
+			}
+
+			return nil
+		},
+	}
+
+	// Not named cancel: that would reassign the readiness timeout's cancel from
+	// above, whose deferred call is already bound to the old value.
+	serveCtx, serveCancel := context.WithCancel(context.Background())
+	a.shutdownCancel = serveCancel
+	a.serveDone = make(chan struct{})
+
 	// As the following code is blocking, run it in a goroutine.
 	go func() {
+		defer close(a.serveDone)
+
 		var err error
 		if a.tlsCertFile != "" && a.tlsKeyFile != "" {
 			// Start an HTTPS server (supports HTTP/2).
-			err = a.srv.StartTLS(fmt.Sprintf("%s:%d", a.bindIp, a.port), a.tlsCertFile, a.tlsKeyFile)
+			err = startConfig.StartTLS(serveCtx, a.srv, a.tlsCertFile, a.tlsKeyFile)
 		} else {
 			// Start an HTTP/2 Cleartext (non-HTTPS) server.
-			server := &http2.Server{}
-			err = a.srv.StartH2CServer(fmt.Sprintf("%s:%d", a.bindIp, a.port), server)
+			err = startConfig.Start(serveCtx, a.srv)
 		}
-		if !errors.Is(err, http.ErrServerClosed) {
+		if err != nil && !errors.Is(err, http.ErrServerClosed) {
 			a.logger.ErrorContext(context.Background(), err.Error())
 		}
 	}()
@@ -697,6 +790,26 @@ func (a *Api) StartupMessage() string {
 	return fmt.Sprintf("server started on %s:%d", ip, a.port)
 }
 
+// shutdown triggers the server's graceful shutdown and waits for it to
+// complete, or for ctx to be done. Cancelling the serve context is what Echo v5
+// exposes in place of Echo.Shutdown: [echo.StartConfig] shuts the server down
+// on its own deadline, so the shutdown proceeds even when ctx is already done.
+func (a *Api) shutdown(ctx context.Context) error {
+	if a.shutdownCancel == nil {
+		// Start never ran, so there is nothing to shut down.
+		return nil
+	}
+
+	a.shutdownCancel()
+
+	select {
+	case <-a.serveDone:
+		return nil
+	case <-ctx.Done():
+		return ctx.Err()
+	}
+}
+
 // Stop stops the HTTP server.
 func (a *Api) Stop(ctx context.Context) error {
 	for {
@@ -706,7 +819,7 @@ func (a *Api) Stop(ctx context.Context) error {
 		}
 		select {
 		case <-ctx.Done():
-			return a.srv.Shutdown(ctx)
+			return a.shutdown(ctx)
 		default:
 			a.logger.DebugContext(ctx, fmt.Sprintf("%d asynchronous requests", count))
 			if count > 0 {
@@ -714,7 +827,7 @@ func (a *Api) Stop(ctx context.Context) error {
 				continue
 			}
 			a.logger.DebugContext(ctx, "no more asynchronous requests, continue with shutdown")
-			err := a.srv.Shutdown(ctx)
+			err := a.shutdown(ctx)
 			if err != nil {
 				return fmt.Errorf("shutdown: %w", err)
 			}

pkg/modules/api/api_test.go

@@ -1,6 +1,8 @@
 package api
 
 import (
+	"bytes"
+	"log/slog"
 	"strings"
 	"testing"
 )
@@ -65,3 +67,68 @@ func TestApi_Validate_Auth(t *testing.T) {
 		})
 	}
 }
+
+func TestApi_warnInsecureDebugRoute(t *testing.T) {
+	for _, tc := range []struct {
+		scenario     string
+		api          Api
+		expectWarn   bool
+		expectFields []string
+	}{
+		{
+			scenario:     "debug route on with no auth warns",
+			api:          Api{enableDebugRoute: true},
+			expectWarn:   true,
+			expectFields: []string{"--api-enable-debug-route", "API_ENABLE_DEBUG_ROUTE", "--api-enable-basic-auth", "API_ENABLE_BASIC_AUTH", "--api-enable-oidc-auth", "API_ENABLE_OIDC_AUTH"},
+		},
+		{
+			scenario:   "debug route off is silent",
+			api:        Api{enableDebugRoute: false},
+			expectWarn: false,
+		},
+		{
+			scenario:   "basic auth silences it",
+			api:        Api{enableDebugRoute: true, basicAuthUsername: "foo"},
+			expectWarn: false,
+		},
+		{
+			scenario:   "oidc silences it",
+			api:        Api{enableDebugRoute: true, oidcEnabled: true},
+			expectWarn: false,
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			buf := new(bytes.Buffer)
+			tc.api.logger = slog.New(slog.NewJSONHandler(buf, &slog.HandlerOptions{Level: slog.LevelWarn}))
+
+			tc.api.warnInsecureDebugRoute()
+
+			logged := buf.String()
+			if !tc.expectWarn {
+				if logged != "" {
+					t.Fatalf("expected no warning, got: %s", logged)
+				}
+				return
+			}
+
+			if logged == "" {
+				t.Fatal("expected a warning, got none")
+			}
+			// Every flag named must carry its environment variable.
+			for _, want := range tc.expectFields {
+				if !strings.Contains(logged, want) {
+					t.Fatalf("warning does not mention %q: %s", want, logged)
+				}
+			}
+			if strings.Contains(logged, "—") {
+				t.Fatalf("warning must not contain an em dash: %s", logged)
+			}
+		})
+	}
+}
+
+// The warning reads a.logger, which is nil until Provision assigns it.
+func TestApi_warnInsecureDebugRoute_NilLoggerDoesNotPanic(t *testing.T) {
+	api := Api{enableDebugRoute: true}
+	api.warnInsecureDebugRoute()
+}

pkg/modules/api/context.go

@@ -18,7 +18,7 @@ import (
 
 	"github.com/google/uuid"
 	"github.com/hashicorp/go-retryablehttp"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 	"github.com/mholt/archives"
 	"go.opentelemetry.io/otel"
 	"go.opentelemetry.io/otel/codes"
@@ -51,8 +51,26 @@ type Context struct {
 	outputPaths    []string
 	cancelled      bool
 
+	// fileOrder records the order files were received in, keyed by disk path.
+	// It breaks ties when two uploads share an original filename, so that
+	// de-duplicated files keep their upload order instead of being ordered by
+	// the suffix uniqueFilename added.
+	fileOrder map[string]int
+
+	// fileBase maps a disk path to the original filename as received, before
+	// de-duplication. Sorting on it keeps a de-duplicated file next to its
+	// twin rather than wherever its numbered name would land.
+	fileBase map[string]string
+
+	// outputFilename is the sanitized Gotenberg-Output-Filename header,
+	// snapshotted while the [echo.Context] is still live. Echo returns that
+	// context to a pool as soon as the handler returns, and an asynchronous
+	// conversion outlives it, so reading the header from the pooled store later
+	// yields whichever request happens to own it by then.
+	outputFilename string
+
 	logger     *slog.Logger
-	echoCtx    echo.Context
+	echoCtx    *echo.Context
 	mkdirAll   gotenberg.MkdirAll
 	pathRename gotenberg.PathRename
 	context.Context
@@ -80,6 +98,48 @@ func (t *trackingReader) Read(p []byte) (int, error) {
 	return n, nil
 }
 
+// errTooManyDownloadFromEntries is returned by [decodeDownloadFrom] when the
+// array holds more entries than the configured maximum.
+var errTooManyDownloadFromEntries = errors.New("too many downloadFrom entries")
+
+// decodeDownloadFrom decodes the downloadFrom form field, refusing to
+// accumulate more than maxEntries. A maxEntries of 0 means no limit.
+//
+// It decodes element by element rather than calling [json.Unmarshal] on the
+// whole value. A compact array such as "[{},{},{}]" costs three bytes per
+// entry on the wire and expands to roughly seventy times that once
+// unmarshalled, so counting the entries afterwards is too late to bound the
+// allocation. Streaming keeps the cost proportional to maxEntries no matter
+// how long the array is.
+func decodeDownloadFrom(raw string, maxEntries int) ([]downloadFrom, error) {
+	dec := json.NewDecoder(strings.NewReader(raw))
+
+	token, err := dec.Token()
+	if err != nil {
+		return nil, err
+	}
+	if delim, ok := token.(json.Delim); !ok || delim != '[' {
+		return nil, fmt.Errorf("expected a JSON array, got '%v'", token)
+	}
+
+	var dls []downloadFrom
+	for dec.More() {
+		if maxEntries > 0 && len(dls) >= maxEntries {
+			return nil, errTooManyDownloadFromEntries
+		}
+
+		var dl downloadFrom
+		err = dec.Decode(&dl)
+		if err != nil {
+			return nil, err
+		}
+
+		dls = append(dls, dl)
+	}
+
+	return dls, nil
+}
+
 type downloadFrom struct {
 	// Url is the URL to download a file from.
 	Url string `json:"url"`
@@ -98,7 +158,7 @@ type downloadFrom struct {
 }
 
 // newContext returns a [Context] by parsing a "multipart/form-data" request.
-func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSystem, timeout time.Duration, bodyLimit int64, downloadFromCfg downloadFromConfig) (*Context, context.CancelFunc, error) {
+func newContext(echoCtx *echo.Context, logger *slog.Logger, fs *gotenberg.FileSystem, timeout time.Duration, bodyLimit int64, downloadFromCfg downloadFromConfig) (*Context, context.CancelFunc, error) {
 	processCtx, processCancel := context.WithTimeout(echoCtx.Request().Context(), timeout)
 
 	// We want to make sure the multipart/form-data does not exceed a given
@@ -117,14 +177,18 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 		return nil
 	}
 
+	// Snapshot now, while echoCtx still belongs to this request.
+	outputFilename, _ := echoCtx.Get("outputFilename").(string)
+
 	ctx := &Context{
-		outputPaths: make([]string, 0),
-		cancelled:   false,
-		logger:      logger,
-		echoCtx:     echoCtx,
-		mkdirAll:    new(gotenberg.OsMkdirAll),
-		pathRename:  new(gotenberg.OsPathRename),
-		Context:     processCtx,
+		outputPaths:    make([]string, 0),
+		cancelled:      false,
+		outputFilename: outputFilename,
+		logger:         logger,
+		echoCtx:        echoCtx,
+		mkdirAll:       new(gotenberg.OsMkdirAll),
+		pathRename:     new(gotenberg.OsPathRename),
+		Context:        processCtx,
 	}
 
 	// A custom cancel function which removes the context's working directory
@@ -213,8 +277,13 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 	// any.
 	raw, ok := ctx.values["downloadFrom"]
 	if !downloadFromCfg.disable && ok {
-		var dls []downloadFrom
-		err = json.Unmarshal([]byte(raw[0]), &dls)
+		dls, err := decodeDownloadFrom(raw[0], downloadFromCfg.maxEntries)
+		if errors.Is(err, errTooManyDownloadFromEntries) {
+			return nil, cancel, WrapError(
+				fmt.Errorf("decode downloadFrom: %w", err),
+				NewSentinelHttpError(http.StatusBadRequest, fmt.Sprintf("Invalid 'downloadFrom' form field value: too many entries, the maximum is %d", downloadFromCfg.maxEntries)),
+			)
+		}
 		if err != nil {
 			return nil, cancel, WrapError(
 				fmt.Errorf("unmarshal json: %w", err),
@@ -232,6 +301,13 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 		results := make([]downloadFromResult, len(dls))
 
 		eg, _ := errgroup.WithContext(ctx)
+		// Bound the number of in-flight downloads. Each entry allocates a
+		// retryable client, an outbound transport, a span, and logger state,
+		// so an unbounded array would otherwise exhaust process memory. A
+		// value of 0 keeps the fan-out unbounded.
+		if downloadFromCfg.maxConcurrency > 0 {
+			eg.SetLimit(downloadFromCfg.maxConcurrency)
+		}
 		for i, dl := range dls {
 			eg.Go(func() error {
 				deadline, ok := ctx.Deadline()
@@ -263,7 +339,12 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 
 				logger.DebugContext(dlCtx, fmt.Sprintf("download file from '%s'", dl.Url))
 
-				req, err := retryablehttp.NewRequest(http.MethodGet, dl.Url, nil)
+				// The request must carry dlCtx: retryablehttp.NewRequest builds
+				// on context.Background(), and its wait between attempts is a
+				// select on the request context, so a contextless request cannot
+				// be interrupted by --api-timeout (env API_TIMEOUT) or by the
+				// caller going away.
+				req, err := retryablehttp.NewRequestWithContext(dlCtx, http.MethodGet, dl.Url, nil)
 				if err != nil {
 					dlSpan.RecordError(err)
 					dlSpan.SetStatus(codes.Error, err.Error())
@@ -286,14 +367,28 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 					}
 				}
 
+				// Entries are serialized by the concurrency limit above, so a
+				// late one can start after the deadline has already passed.
+				// Fail closed rather than derive a non-positive timeout, which
+				// [http.Client] reads as no deadline at all.
+				remaining := time.Until(deadline)
+				if remaining <= 0 {
+					dlSpan.RecordError(context.DeadlineExceeded)
+					dlSpan.SetStatus(codes.Error, context.DeadlineExceeded.Error())
+					dlSpan.End()
+					return fmt.Errorf("download file from '%s': %w", dl.Url, context.DeadlineExceeded)
+				}
+
 				client := &retryablehttp.Client{
-					HTTPClient:   gotenberg.NewOutboundHttpClient(time.Until(deadline), downloadFromCfg.allowList, downloadFromCfg.denyList, downloadFromCfg.enableEnvironmentProxy, ipOpts...),
+					HTTPClient:   gotenberg.NewOutboundHttpClient(remaining, downloadFromCfg.allowList, downloadFromCfg.denyList, downloadFromCfg.enableEnvironmentProxy, ipOpts...),
 					RetryMax:     downloadFromCfg.maxRetry,
 					RetryWaitMin: time.Duration(1) * time.Second,
-					RetryWaitMax: time.Until(deadline),
+					RetryWaitMax: remaining,
 					Logger:       gotenberg.NewLeveledLogger(logger),
 					CheckRetry:   retryablehttp.DefaultRetryPolicy,
-					Backoff:      retryablehttp.DefaultBackoff,
+					// Not DefaultBackoff: it hands a hostile origin control of
+					// the wait via Retry-After.
+					Backoff: gotenberg.ClampedBackoff,
 				}
 
 				resp, err := client.Do(req)
@@ -301,6 +396,17 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 					dlSpan.RecordError(err)
 					dlSpan.SetStatus(codes.Error, err.Error())
 					dlSpan.End()
+
+					// A redirect target is filtered inside the client, so the
+					// policy verdict surfaces here rather than from the
+					// pre-flight above. Keep it out of the response: the first
+					// hop answers a filtered URL with a generic 403, and a
+					// later hop must not describe the allow-list, the deny-list
+					// or the IP policy instead.
+					if errors.Is(err, gotenberg.ErrFiltered) {
+						return fmt.Errorf("download file from '%s': %w", dl.Url, err)
+					}
+
 					return WrapError(
 						fmt.Errorf("download file from to '%s': %w", dl.Url, err),
 						NewSentinelHttpError(http.StatusBadRequest, fmt.Sprintf("Unable to download file from '%s': %s", dl.Url, err)),
@@ -374,7 +480,7 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 				// Use a UUID-based name on disk to avoid filesystem
 				// NAME_MAX limits with long filenames.
 				// See: https://github.com/gotenberg/gotenberg/issues/1500.
-				safeName := uuid.New().String() + filepath.Ext(filename)
+				safeName := uuid.New().String() + safeExt(filename)
 				path := fmt.Sprintf("%s/%s", ctx.dirPath, safeName)
 
 				out, err := os.Create(path)
@@ -428,18 +534,20 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 		}
 
 		for _, r := range results {
-			ctx.files[r.filename] = r.path
-			ctx.diskToOriginal[r.path] = r.filename
+			filename := ctx.uniqueFilename(r.filename)
+			ctx.files[filename] = r.path
+			ctx.diskToOriginal[r.path] = filename
+			ctx.trackFileOrder(r.path, r.filename)
 			if r.formField != "" {
 				ctx.filesByField[r.formField] = append(ctx.filesByField[r.formField], r.path)
 			}
 		}
 	}
 
-	copyToDisk := func(fh *multipart.FileHeader) error {
+	copyToDisk := func(fh *multipart.FileHeader) (string, error) {
 		in, err := fh.Open()
 		if err != nil {
-			return fmt.Errorf("open multipart file: %w", err)
+			return "", fmt.Errorf("open multipart file: %w", err)
 		}
 
 		defer func() {
@@ -462,12 +570,12 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 		// Use a UUID-based name on disk to avoid filesystem
 		// NAME_MAX limits with long filenames.
 		// See: https://github.com/gotenberg/gotenberg/issues/1500.
-		safeName := uuid.New().String() + filepath.Ext(filename)
+		safeName := uuid.New().String() + safeExt(filename)
 		path := fmt.Sprintf("%s/%s", ctx.dirPath, safeName)
 
 		out, err := os.Create(path)
 		if err != nil {
-			return fmt.Errorf("create local file: %w", err)
+			return "", fmt.Errorf("create local file: %w", err)
 		}
 		defer func() {
 			err := out.Close()
@@ -478,26 +586,28 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 
 		_, err = io.Copy(out, reader)
 		if err != nil {
-			return fmt.Errorf("copy multipart file to local file: %w", err)
+			return "", fmt.Errorf("copy multipart file to local file: %w", err)
 		}
 
+		base := filename
+		filename = ctx.uniqueFilename(filename)
 		ctx.files[filename] = path
 		ctx.diskToOriginal[path] = filename
+		ctx.trackFileOrder(path, base)
 
-		return nil
+		return filename, nil
 	}
 
 	// Then, copy the form files, if any.
 	for fieldName, files := range form.File {
 		for _, fh := range files {
-			err = copyToDisk(fh)
-			if err != nil {
-				return ctx, cancel, fmt.Errorf("copy to disk: %w", err)
+			filename, errCopy := copyToDisk(fh)
+			if errCopy != nil {
+				return ctx, cancel, fmt.Errorf("copy to disk: %w", errCopy)
 			}
-			// Track files by field name
-			filename := sanitizeFilename(fh.Filename)
-			filePath := ctx.files[filename]
-			ctx.filesByField[fieldName] = append(ctx.filesByField[fieldName], filePath)
+			// Track files by field name, under the name copyToDisk actually
+			// stored, which may be a de-duplicated variant.
+			ctx.filesByField[fieldName] = append(ctx.filesByField[fieldName], ctx.files[filename])
 		}
 	}
 
@@ -512,9 +622,9 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 		if symlinkPath == diskPath {
 			continue
 		}
-		err = os.Symlink(filepath.Base(diskPath), symlinkPath)
-		if err != nil {
-			logger.DebugContext(context.Background(), fmt.Sprintf("skip symlink for '%s': %s", originalName, err))
+		errSymlink := os.Symlink(filepath.Base(diskPath), symlinkPath)
+		if errSymlink != nil {
+			logger.DebugContext(context.Background(), fmt.Sprintf("skip symlink for '%s': %s", originalName, errSymlink))
 		}
 	}
 
@@ -523,7 +633,10 @@ func newContext(echoCtx echo.Context, logger *slog.Logger, fs *gotenberg.FileSys
 	ctx.Log().DebugContext(ctx, fmt.Sprintf("form files by field: %+v", ctx.filesByField))
 	ctx.Log().DebugContext(ctx, fmt.Sprintf("total bytes: %d", totalBytesRead.Load()))
 
-	return ctx, cancel, err
+	// Explicitly nil: the best-effort symlink loop above must not decide the
+	// outcome of the request. Its failure used to escape here as a bare 500,
+	// non-deterministically, because ctx.files iterates in random order.
+	return ctx, cancel, nil
 }
 
 // Request returns the [http.Request].
@@ -538,6 +651,8 @@ func (ctx *Context) FormData() *FormData {
 		files:          ctx.files,
 		filesByField:   ctx.filesByField,
 		diskToOriginal: ctx.diskToOriginal,
+		fileOrder:      ctx.fileOrder,
+		fileBase:       ctx.fileBase,
 		errors:         nil,
 	}
 }
@@ -578,7 +693,7 @@ func (ctx *Context) GeneratePath(extension string) string {
 // limits but registers the given filename so that [Context.OriginalFilename]
 // can resolve it. It does not create a file.
 func (ctx *Context) GeneratePathFromFilename(filename string) string {
-	safeName := uuid.New().String() + filepath.Ext(filename)
+	safeName := uuid.New().String() + safeExt(filename)
 	path := fmt.Sprintf("%s/%s", ctx.dirPath, safeName)
 	ctx.diskToOriginal[path] = filename
 	return path
@@ -681,15 +796,72 @@ func (ctx *Context) BuildOutputFile() (string, error) {
 // OutputFilename returns the filename based on the given output path or the
 // "Gotenberg-Output-Filename" header's value.
 func (ctx *Context) OutputFilename(outputPath string) string {
-	filename := ctx.echoCtx.Get("outputFilename").(string)
-
-	if filename == "" {
+	if ctx.outputFilename == "" {
 		return ctx.OriginalFilename(outputPath)
 	}
 
+	filename := ctx.outputFilename
+
 	return fmt.Sprintf("%s%s", filename, filepath.Ext(outputPath))
 }
 
+// maxDiskExtLength bounds the extension copied onto a UUID-based disk name.
+// The UUID stem is 36 characters, so a longer extension risks NAME_MAX, which
+// is 255 on ext4 and overlayfs. The untruncated name is kept in
+// [Context.diskToOriginal], which never reaches the filesystem.
+const maxDiskExtLength = 32
+
+// safeExt returns the extension to append to a UUID-based disk name. It drops
+// an extension too long to be safe rather than let [os.Create] fail with
+// ENAMETOOLONG, which surfaced to the caller as a bare 500.
+func safeExt(filename string) string {
+	ext := filepath.Ext(filename)
+	if len(ext) > maxDiskExtLength {
+		return ""
+	}
+
+	return ext
+}
+
+// uniqueFilename returns filename, or a numbered variant of it when the
+// request already carries a file by that name.
+//
+// Uploads are keyed by their sanitized original filename, so two files sharing
+// one name used to collide: the second overwrote the first and only one
+// reached the conversion, while both stayed on disk and counted against the
+// body limit. Sanitizing strips directories, so "a/doc.pdf" and "b/doc.pdf"
+// collide too.
+func (ctx *Context) uniqueFilename(filename string) string {
+	_, exists := ctx.files[filename]
+	if !exists {
+		return filename
+	}
+
+	ext := filepath.Ext(filename)
+	stem := strings.TrimSuffix(filename, ext)
+
+	for i := 2; ; i++ {
+		candidate := fmt.Sprintf("%s (%d)%s", stem, i, ext)
+		_, exists = ctx.files[candidate]
+		if !exists {
+			return candidate
+		}
+	}
+}
+
+// trackFileOrder records where a file arrived in the request and the filename
+// it arrived under, so [FormData.paths] can order it the way the caller sent
+// it.
+func (ctx *Context) trackFileOrder(path, base string) {
+	if ctx.fileOrder == nil {
+		ctx.fileOrder = make(map[string]int)
+		ctx.fileBase = make(map[string]string)
+	}
+
+	ctx.fileOrder[path] = len(ctx.fileOrder)
+	ctx.fileBase[path] = base
+}
+
 // sanitizeFilename strips path separators (including backslashes, which
 // [filepath.Base] ignores on Linux) and control characters from a
 // caller-supplied filename, then NFC-normalizes the result. This prevents a

pkg/modules/api/context_test.go

@@ -4,17 +4,23 @@ import (
 	"bytes"
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"log/slog"
 	"mime/multipart"
 	"net/http"
 	"net/http/httptest"
 	"os"
+	"regexp"
+	"runtime"
+	"strings"
 	"sync"
+	"sync/atomic"
 	"testing"
 	"time"
 
-	"github.com/labstack/echo/v4"
+	"github.com/dlclark/regexp2/v2"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
@@ -209,6 +215,137 @@ func TestNewContext_DownloadFromConcurrentMapWrites(t *testing.T) {
 	}
 }
 
+// An oversized downloadFrom array must be rejected at the trust boundary with
+// a 400, before any download goroutine is spawned.
+// https://github.com/gotenberg/gotenberg/security/advisories/GHSA-6vqw-2jgm-4x88
+func TestNewContext_DownloadFromMaxEntries(t *testing.T) {
+	var hits atomic.Int64
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		hits.Add(1)
+		w.Header().Set("Content-Disposition", `attachment; filename="download.txt"`)
+		_, _ = w.Write([]byte("downloaded"))
+	}))
+	defer server.Close()
+
+	dls := make([]downloadFrom, 3)
+	for i := range dls {
+		dls[i] = downloadFrom{Url: fmt.Sprintf("%s/file?i=%d", server.URL, i)}
+	}
+
+	payload, err := json.Marshal(dls)
+	if err != nil {
+		t.Fatalf("marshal downloadFrom payload: %v", err)
+	}
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err = writer.WriteField("downloadFrom", string(payload))
+	if err != nil {
+		t.Fatalf("write downloadFrom field: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+	downloadFromCfg := downloadFromConfig{maxEntries: 2}
+
+	_, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromCfg)
+	if cancel != nil {
+		defer cancel()
+	}
+	if err == nil {
+		t.Fatal("newContext returned no error, want a 400 for too many entries")
+	}
+
+	var httpErr HttpError
+	if !errors.As(err, &httpErr) {
+		t.Fatalf("error %v is not an HttpError", err)
+	}
+	if status, _ := httpErr.HttpError(); status != http.StatusBadRequest {
+		t.Fatalf("HTTP status = %d, want %d", status, http.StatusBadRequest)
+	}
+	if got := hits.Load(); got != 0 {
+		t.Fatalf("server hits = %d, want 0 (rejected before any download)", got)
+	}
+}
+
+// The number of in-flight downloadFrom fetches must never exceed the
+// configured concurrency limit, regardless of array length.
+// https://github.com/gotenberg/gotenberg/security/advisories/GHSA-6vqw-2jgm-4x88
+func TestNewContext_DownloadFromMaxConcurrency(t *testing.T) {
+	const (
+		downloads      = 8
+		maxConcurrency = 2
+	)
+
+	var current, peak atomic.Int64
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		inFlight := current.Add(1)
+		for {
+			observed := peak.Load()
+			if inFlight <= observed || peak.CompareAndSwap(observed, inFlight) {
+				break
+			}
+		}
+		time.Sleep(20 * time.Millisecond)
+		current.Add(-1)
+
+		filename := fmt.Sprintf("download-%s.txt", r.URL.Query().Get("i"))
+		w.Header().Set("Content-Disposition", fmt.Sprintf(`attachment; filename="%s"`, filename))
+		_, _ = w.Write([]byte("downloaded"))
+	}))
+	defer server.Close()
+
+	dls := make([]downloadFrom, downloads)
+	for i := range dls {
+		dls[i] = downloadFrom{Url: fmt.Sprintf("%s/file?i=%d", server.URL, i)}
+	}
+
+	payload, err := json.Marshal(dls)
+	if err != nil {
+		t.Fatalf("marshal downloadFrom payload: %v", err)
+	}
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err = writer.WriteField("downloadFrom", string(payload))
+	if err != nil {
+		t.Fatalf("write downloadFrom field: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+	downloadFromCfg := downloadFromConfig{maxConcurrency: maxConcurrency}
+
+	ctx, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromCfg)
+	if err != nil {
+		t.Fatalf("newContext returned error: %v", err)
+	}
+	defer cancel()
+
+	if got := len(ctx.files); got != downloads {
+		t.Fatalf("downloaded files = %d, want %d", got, downloads)
+	}
+	if got := peak.Load(); got > maxConcurrency {
+		t.Fatalf("peak concurrency = %d, want <= %d", got, maxConcurrency)
+	}
+}
+
 func TestSanitizeFilename(t *testing.T) {
 	for _, tc := range []struct {
 		scenario string
@@ -281,3 +418,487 @@ func TestContext_FileCount(t *testing.T) {
 		t.Errorf("expected 3 files, got %d", got)
 	}
 }
+
+// A hostile origin must not choose how long Gotenberg waits.
+// [retryablehttp.DefaultBackoff] returns a Retry-After header verbatim for 429
+// and 503, and the wait between attempts is a select on the request context.
+// Building the request without a context therefore pinned the goroutine, its
+// connection, and its working directory for the attacker's chosen duration,
+// well past --api-timeout (env API_TIMEOUT).
+func TestNewContext_DownloadFromHostileRetryAfterIsBounded(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Retry-After", "3600")
+		w.WriteHeader(http.StatusTooManyRequests)
+	}))
+	defer server.Close()
+
+	payload, err := json.Marshal([]downloadFrom{{Url: server.URL + "/file"}})
+	if err != nil {
+		t.Fatalf("marshal downloadFrom payload: %v", err)
+	}
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err = writer.WriteField("downloadFrom", string(payload))
+	if err != nil {
+		t.Fatalf("write downloadFrom field: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	const timeout = 500 * time.Millisecond
+
+	start := time.Now()
+	_, cancel, err := newContext(echoCtx, logger, fs, timeout, 0, downloadFromConfig{maxRetry: 2})
+	elapsed := time.Since(start)
+	if cancel != nil {
+		defer cancel()
+	}
+
+	if err == nil {
+		t.Fatal("expected newContext to fail against an origin that only answers 429")
+	}
+	// Generous: the deadline is 500ms and Retry-After asks for an hour. Any
+	// value in seconds means the remote is still in control.
+	if elapsed > 10*time.Second {
+		t.Fatalf("newContext took %s with Retry-After 3600; --api-timeout must bound it", elapsed)
+	}
+}
+
+// An entry that starts after the deadline has passed must fail closed. It used
+// to derive a negative client timeout, which [http.Client] reads as no
+// deadline at all, leaving the download unbounded.
+func TestNewContext_DownloadFromExpiredBudgetFailsClosed(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		<-r.Context().Done()
+	}))
+	defer server.Close()
+
+	// Two entries, serialized by the concurrency limit, so the second one
+	// starts once the first has burned the whole budget.
+	payload, err := json.Marshal([]downloadFrom{
+		{Url: server.URL + "/first"},
+		{Url: server.URL + "/second"},
+	})
+	if err != nil {
+		t.Fatalf("marshal downloadFrom payload: %v", err)
+	}
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err = writer.WriteField("downloadFrom", string(payload))
+	if err != nil {
+		t.Fatalf("write downloadFrom field: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	done := make(chan error, 1)
+	go func() {
+		_, cancel, err := newContext(echoCtx, logger, fs, 400*time.Millisecond, 0, downloadFromConfig{
+			maxRetry:       0,
+			maxConcurrency: 1,
+		})
+		if cancel != nil {
+			cancel()
+		}
+		done <- err
+	}()
+
+	select {
+	case err := <-done:
+		if err == nil {
+			t.Fatal("expected newContext to fail against a stalling origin")
+		}
+	case <-time.After(15 * time.Second):
+		t.Fatal("newContext never returned: an entry starting past the deadline built an unbounded client")
+	}
+}
+
+func TestDecodeDownloadFrom(t *testing.T) {
+	for _, tc := range []struct {
+		scenario   string
+		raw        string
+		maxEntries int
+		expectErr  error
+		expectLen  int
+	}{
+		{"empty array", `[]`, 10, nil, 0},
+		{"under the limit", `[{"url":"http://a"},{"url":"http://b"}]`, 10, nil, 2},
+		{"exactly the limit", `[{"url":"http://a"},{"url":"http://b"}]`, 2, nil, 2},
+		{"over the limit", `[{"url":"http://a"},{"url":"http://b"}]`, 1, errTooManyDownloadFromEntries, 0},
+		{"no limit", `[{"url":"http://a"},{"url":"http://b"}]`, 0, nil, 2},
+		{"not an array", `{"url":"http://a"}`, 10, nil, 0},
+		{"malformed", `[{"url":`, 10, nil, 0},
+		{"not json", `nope`, 10, nil, 0},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			dls, err := decodeDownloadFrom(tc.raw, tc.maxEntries)
+
+			if tc.expectErr != nil {
+				if !errors.Is(err, tc.expectErr) {
+					t.Fatalf("error = %v, want %v", err, tc.expectErr)
+				}
+				return
+			}
+			if tc.scenario == "not an array" || tc.scenario == "malformed" || tc.scenario == "not json" {
+				if err == nil {
+					t.Fatalf("expected an error for %q", tc.raw)
+				}
+				return
+			}
+			if err != nil {
+				t.Fatalf("unexpected error: %v", err)
+			}
+			if len(dls) != tc.expectLen {
+				t.Fatalf("decoded %d entries, want %d", len(dls), tc.expectLen)
+			}
+		})
+	}
+}
+
+// A compact array costs three bytes per entry on the wire and expands by
+// roughly seventy times once unmarshalled. Decoding must stop at the limit
+// rather than materialize the whole array and count afterwards.
+func TestDecodeDownloadFrom_StopsBeforeMaterializingTheArray(t *testing.T) {
+	const entries = 2_000_000
+
+	raw := "[" + strings.Repeat("{},", entries) + "{}]"
+
+	var before, after runtime.MemStats
+	runtime.GC()
+	runtime.ReadMemStats(&before)
+
+	_, err := decodeDownloadFrom(raw, 1000)
+
+	runtime.ReadMemStats(&after)
+
+	if !errors.Is(err, errTooManyDownloadFromEntries) {
+		t.Fatalf("error = %v, want errTooManyDownloadFromEntries", err)
+	}
+
+	// json.Unmarshal on the same input allocates hundreds of MiB. Bounded
+	// decoding should stay in the low single-digit MiB, so this threshold is
+	// deliberately loose and still fails loudly on a regression.
+	allocated := after.TotalAlloc - before.TotalAlloc
+	if allocated > 32<<20 {
+		t.Fatalf("decoding allocated %d MiB for a %d-entry array, want the limit to bound it", allocated>>20, entries)
+	}
+	t.Logf("allocated %d KiB decoding a %d-entry array with a limit of 1000", allocated>>10, entries)
+}
+
+// An asynchronous conversion outlives the [echo.Context]. Echo returns that
+// context to a sync.Pool as soon as the handler returns, and
+// outputFilenameMiddleware runs in srv.Pre on every request, including
+// /health, so a later request overwrites the store. Reading the output
+// filename from it after the fact returned another caller's value.
+func TestContext_OutputFilename_SurvivesEchoContextRecycling(t *testing.T) {
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err := writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	// What outputFilenameMiddleware does for this request.
+	echoCtx.Set("outputFilename", "victim")
+
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	ctx, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{disable: true})
+	if err != nil {
+		t.Fatalf("newContext returned error: %v", err)
+	}
+	defer cancel()
+
+	// Echo recycles the context and another request claims the store.
+	echoCtx.Set("outputFilename", "attacker-controlled")
+
+	if got := ctx.OutputFilename("/tmp/out.pdf"); got != "victim.pdf" {
+		t.Fatalf("OutputFilename = %q, want %q", got, "victim.pdf")
+	}
+}
+
+// A recycled context has a nil store, so the previous unguarded type assertion
+// could panic. The snapshot must tolerate an absent value.
+func TestContext_OutputFilename_NoHeader(t *testing.T) {
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err := writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	// No Set call at all: the store holds nothing for "outputFilename".
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	ctx, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{disable: true})
+	if err != nil {
+		t.Fatalf("newContext returned error: %v", err)
+	}
+	defer cancel()
+
+	if got := ctx.OutputFilename("/tmp/out.pdf"); got != "out.pdf" {
+		t.Fatalf("OutputFilename = %q, want the original filename %q", got, "out.pdf")
+	}
+}
+
+func TestSafeExt(t *testing.T) {
+	for _, tc := range []struct {
+		scenario string
+		filename string
+		want     string
+	}{
+		{"ordinary extension", "report.pdf", ".pdf"},
+		{"no extension", "report", ""},
+		{"at the limit", "a." + strings.Repeat("x", maxDiskExtLength-1), "." + strings.Repeat("x", maxDiskExtLength-1)},
+		{"over the limit is dropped", "a." + strings.Repeat("x", 300), ""},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			got := safeExt(tc.filename)
+			if got != tc.want {
+				t.Fatalf("safeExt(%q) = %q, want %q", tc.filename, got, tc.want)
+			}
+			// A UUID stem is 36 characters. The whole disk name must stay
+			// under NAME_MAX.
+			if len(got)+36 > 255 {
+				t.Fatalf("disk name would be %d characters, over NAME_MAX", len(got)+36)
+			}
+		})
+	}
+}
+
+// An upload whose extension exceeds NAME_MAX used to fail os.Create and return
+// a bare 500. The extension is bounded, and the original name survives in
+// diskToOriginal.
+func TestNewContext_LongExtensionIsAccepted(t *testing.T) {
+	filename := "invoice." + strings.Repeat("x", 300)
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	part, err := writer.CreateFormFile("files", filename)
+	if err != nil {
+		t.Fatalf("create multipart file: %v", err)
+	}
+	_, err = part.Write([]byte("%PDF-1.4"))
+	if err != nil {
+		t.Fatalf("write multipart file: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	ctx, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{disable: true})
+	if cancel != nil {
+		defer cancel()
+	}
+	if err != nil {
+		t.Fatalf("newContext returned error for a long extension: %v", err)
+	}
+	if got := len(ctx.files); got != 1 {
+		t.Fatalf("files = %d, want 1", got)
+	}
+}
+
+// A filename that cannot become a symlink (too long, "..", "/") must not fail
+// the request. The symlink loop is best-effort, but its error escaped through
+// the shared err variable, and ctx.files iterates randomly, so byte-identical
+// requests gave different HTTP outcomes.
+func TestNewContext_UnsymlinkableFilenameStillSucceeds(t *testing.T) {
+	for _, filename := range []string{
+		strings.Repeat("a", 300) + ".txt",
+		"..",
+		"/",
+	} {
+		t.Run(filename[:min(len(filename), 12)], func(t *testing.T) {
+			body := new(bytes.Buffer)
+			writer := multipart.NewWriter(body)
+			part, err := writer.CreateFormFile("files", filename)
+			if err != nil {
+				t.Fatalf("create multipart file: %v", err)
+			}
+			_, err = part.Write([]byte("%PDF-1.4"))
+			if err != nil {
+				t.Fatalf("write multipart file: %v", err)
+			}
+			err = writer.Close()
+			if err != nil {
+				t.Fatalf("close multipart writer: %v", err)
+			}
+
+			req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+			req.Header.Set("Content-Type", writer.FormDataContentType())
+
+			echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+			logger := slog.New(slog.DiscardHandler)
+			fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+			_, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{disable: true})
+			if cancel != nil {
+				defer cancel()
+			}
+			if err != nil {
+				t.Fatalf("newContext failed on a best-effort symlink for %q: %v", filename, err)
+			}
+		})
+	}
+}
+
+// Two uploads sharing a filename must both reach the conversion. The second
+// used to overwrite the first in ctx.files, so one file was silently dropped
+// while both stayed on disk and counted against the body limit.
+func TestNewContext_DuplicateFilenamesAreBothKept(t *testing.T) {
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	for _, content := range []string{"FIRST", "SECOND"} {
+		part, err := writer.CreateFormFile("files", "doc.pdf")
+		if err != nil {
+			t.Fatalf("create multipart file: %v", err)
+		}
+		_, err = part.Write([]byte(content))
+		if err != nil {
+			t.Fatalf("write multipart file: %v", err)
+		}
+	}
+	err := writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/pdfengines/merge", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	ctx, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{disable: true})
+	if err != nil {
+		t.Fatalf("newContext returned error: %v", err)
+	}
+	defer cancel()
+
+	if got := len(ctx.files); got != 2 {
+		t.Fatalf("ctx.files = %d entries, want 2: a duplicate filename dropped a file", got)
+	}
+	if got := len(ctx.filesByField["files"]); got != 2 {
+		t.Fatalf("filesByField[files] = %d entries, want 2", got)
+	}
+
+	// The two maps must agree, and both files must be distinct on disk.
+	seen := make(map[string]struct{})
+	for _, path := range ctx.files {
+		if _, ok := ctx.diskToOriginal[path]; !ok {
+			t.Fatalf("path %q has no diskToOriginal entry", path)
+		}
+		seen[path] = struct{}{}
+	}
+	if len(seen) != 2 {
+		t.Fatalf("distinct disk paths = %d, want 2", len(seen))
+	}
+}
+
+// A redirect target is filtered inside the HTTP client, so the policy verdict
+// surfaces from client.Do rather than from the pre-flight check. It used to be
+// interpolated into the response body, so a redirect described the allow-list,
+// the deny-list or the IP policy where the first hop returns a generic 403.
+func TestNewContext_DownloadFromRedirectVerdictStaysGeneric(t *testing.T) {
+	private := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Disposition", `attachment; filename="secret.txt"`)
+		_, _ = w.Write([]byte("internal"))
+	}))
+	defer private.Close()
+
+	redirector := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		http.Redirect(w, r, private.URL+"/secret", http.StatusFound)
+	}))
+	defer redirector.Close()
+
+	payload, err := json.Marshal([]downloadFrom{{Url: redirector.URL + "/start"}})
+	if err != nil {
+		t.Fatalf("marshal downloadFrom payload: %v", err)
+	}
+
+	body := new(bytes.Buffer)
+	writer := multipart.NewWriter(body)
+	err = writer.WriteField("downloadFrom", string(payload))
+	if err != nil {
+		t.Fatalf("write downloadFrom field: %v", err)
+	}
+	err = writer.Close()
+	if err != nil {
+		t.Fatalf("close multipart writer: %v", err)
+	}
+
+	req := httptest.NewRequest(http.MethodPost, "/forms/libreoffice/convert", body)
+	req.Header.Set("Content-Type", writer.FormDataContentType())
+
+	echoCtx := echo.New().NewContext(req, httptest.NewRecorder())
+	logger := slog.New(slog.DiscardHandler)
+	fs := gotenberg.NewFileSystem(new(gotenberg.OsMkdirAll))
+
+	// The first hop is allowed, the redirect target is denied by the deny-list.
+	denyList := []*regexp2.Regexp{regexp2.MustCompile("^"+regexp.QuoteMeta(private.URL), regexp2.None)}
+
+	_, cancel, err := newContext(echoCtx, logger, fs, 10*time.Second, 0, downloadFromConfig{
+		denyList: denyList,
+		maxRetry: 0,
+	})
+	if cancel != nil {
+		defer cancel()
+	}
+	if err == nil {
+		t.Fatal("expected the redirect to a denied host to fail")
+	}
+
+	status, message := ParseError(err)
+	if status != http.StatusForbidden {
+		t.Fatalf("status = %d, want %d: a filtered redirect must answer like a filtered first hop", status, http.StatusForbidden)
+	}
+	if message != http.StatusText(http.StatusForbidden) {
+		t.Fatalf("message = %q, want the generic %q", message, http.StatusText(http.StatusForbidden))
+	}
+	// The response must not name the policy, the pattern, or the blocked host.
+	for _, leak := range []string{"denied list", "allowed list", "non-public", "expression", private.URL} {
+		if strings.Contains(message, leak) {
+			t.Fatalf("response message %q leaks %q", message, leak)
+		}
+	}
+}

pkg/modules/api/formdata.go

@@ -41,6 +41,8 @@ type FormData struct {
 	files          map[string]string
 	filesByField   map[string][]string
 	diskToOriginal map[string]string
+	fileOrder      map[string]int
+	fileBase       map[string]string
 	errors         error
 }
 
@@ -582,24 +584,42 @@ func (form *FormData) paths(extensions []string, target *[]string) *FormData {
 	}
 
 	// See https://github.com/gotenberg/gotenberg/issues/139.
-	originals := make(gotenberg.AlphanumericSort, len(entries))
-	for i, e := range entries {
-		originals[i] = e.original
-	}
-	sort.Sort(originals)
+	//
+	// Sort on the filename as received rather than on the map key. The key
+	// carries the suffix uniqueFilename adds when two uploads share a name,
+	// and that suffix would otherwise decide the order: "doc (2).pdf" sorts
+	// before "doc.pdf". Ordering on the received name keeps the pair adjacent,
+	// and the arrival index breaks the tie, so duplicates merge in the order
+	// the caller sent them. A file with a unique name is unaffected, since its
+	// received name and its key are the same string.
+	sort.SliceStable(entries, func(i, j int) bool {
+		nameI := form.receivedName(entries[i].disk, entries[i].original)
+		nameJ := form.receivedName(entries[j].disk, entries[j].original)
+		if nameI != nameJ {
+			return gotenberg.AlphanumericSort{nameI, nameJ}.Less(0, 1)
+		}
+
+		return form.fileOrder[entries[i].disk] < form.fileOrder[entries[j].disk]
+	})
 
-	// Build a lookup from original name to disk path.
-	lookup := make(map[string]string, len(entries))
 	for _, e := range entries {
-		lookup[e.original] = e.disk
-	}
-	for _, o := range originals {
-		*target = append(*target, lookup[o])
+		*target = append(*target, e.disk)
 	}
 
 	return form
 }
 
+// receivedName returns the filename the file at disk arrived under, before
+// de-duplication, falling back to fallback.
+func (form *FormData) receivedName(disk, fallback string) string {
+	base, ok := form.fileBase[disk]
+	if ok {
+		return base
+	}
+
+	return fallback
+}
+
 // append adds an error to the list of errors.
 func (form *FormData) append(err error) {
 	form.errors = errors.Join(form.errors, err)
@@ -612,7 +632,7 @@ func (form *FormData) mustValue(key string, target any, defaultValue any) *FormD
 	val, ok := form.values[key]
 
 	if !ok || val[0] == "" {
-		switch t := (target).(type) {
+		switch t := target.(type) {
 		case *string:
 			*t = defaultValue.(string)
 		case *bool:
@@ -659,7 +679,7 @@ func (form *FormData) mustMandatoryField(key string, target any) *FormData {
 func (form *FormData) mustAssign(key, value string, target any) *FormData {
 	var err error
 
-	switch t := (target).(type) {
+	switch t := target.(type) {
 	case *string:
 		*t = value
 	case *bool:

pkg/modules/api/formdata_test.go

@@ -1895,3 +1895,81 @@ func TestFormData_Watermarks(t *testing.T) {
 		t.Errorf("expected %+v, got %+v", want, got)
 	}
 }
+
+// De-duplicating a repeated filename must not change merge order. Files with
+// unique names keep exactly the order they had before de-duplication existed,
+// and two files sharing a name merge in the order the caller sent them.
+func TestFormData_paths_DuplicateFilenamesKeepUploadOrder(t *testing.T) {
+	for _, tc := range []struct {
+		scenario string
+		files    map[string]string
+		fileBase map[string]string
+		order    map[string]int
+		want     []string
+	}{
+		{
+			scenario: "unique names sort exactly as before",
+			files:    map[string]string{"b.pdf": "/w/2", "a.pdf": "/w/1", "c.pdf": "/w/3"},
+			fileBase: map[string]string{"/w/1": "a.pdf", "/w/2": "b.pdf", "/w/3": "c.pdf"},
+			order:    map[string]int{"/w/1": 0, "/w/2": 1, "/w/3": 2},
+			want:     []string{"/w/1", "/w/2", "/w/3"},
+		},
+		{
+			scenario: "numeric prefixes still win",
+			files:    map[string]string{"10_x.pdf": "/w/3", "2_x.pdf": "/w/2", "1_x.pdf": "/w/1"},
+			fileBase: map[string]string{"/w/1": "1_x.pdf", "/w/2": "2_x.pdf", "/w/3": "10_x.pdf"},
+			order:    map[string]int{"/w/1": 0, "/w/2": 1, "/w/3": 2},
+			want:     []string{"/w/1", "/w/2", "/w/3"},
+		},
+		{
+			scenario: "duplicates merge in upload order, not suffix order",
+			files:    map[string]string{"doc.pdf": "/w/1", "doc (2).pdf": "/w/2"},
+			fileBase: map[string]string{"/w/1": "doc.pdf", "/w/2": "doc.pdf"},
+			order:    map[string]int{"/w/1": 0, "/w/2": 1},
+			want:     []string{"/w/1", "/w/2"},
+		},
+		{
+			scenario: "duplicates stay adjacent and in position",
+			files: map[string]string{
+				"a.pdf": "/w/1", "doc.pdf": "/w/2", "doc (2).pdf": "/w/3", "z.pdf": "/w/4",
+			},
+			fileBase: map[string]string{
+				"/w/1": "a.pdf", "/w/2": "doc.pdf", "/w/3": "doc.pdf", "/w/4": "z.pdf",
+			},
+			order: map[string]int{"/w/1": 0, "/w/2": 1, "/w/3": 2, "/w/4": 3},
+			want:  []string{"/w/1", "/w/2", "/w/3", "/w/4"},
+		},
+		{
+			scenario: "three copies keep their order",
+			files:    map[string]string{"r.pdf": "/w/1", "r (2).pdf": "/w/2", "r (3).pdf": "/w/3"},
+			fileBase: map[string]string{"/w/1": "r.pdf", "/w/2": "r.pdf", "/w/3": "r.pdf"},
+			order:    map[string]int{"/w/1": 0, "/w/2": 1, "/w/3": 2},
+			want:     []string{"/w/1", "/w/2", "/w/3"},
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			form := &FormData{
+				files:        tc.files,
+				filesByField: map[string][]string{},
+				fileBase:     tc.fileBase,
+				fileOrder:    tc.order,
+			}
+
+			// Map iteration is randomised, so run it repeatedly: an unstable
+			// comparator shows up as a differing result across runs.
+			for range 50 {
+				var got []string
+				form.paths([]string{".pdf"}, &got)
+
+				if len(got) != len(tc.want) {
+					t.Fatalf("paths() returned %d entries, want %d", len(got), len(tc.want))
+				}
+				for i := range got {
+					if got[i] != tc.want[i] {
+						t.Fatalf("paths() = %v, want %v", got, tc.want)
+					}
+				}
+			}
+		})
+	}
+}

pkg/modules/api/middlewares.go

@@ -12,8 +12,8 @@ import (
 
 	"github.com/coreos/go-oidc/v3/oidc"
 	"github.com/google/uuid"
-	"github.com/labstack/echo/v4"
-	"github.com/labstack/echo/v4/middleware"
+	"github.com/labstack/echo/v5"
+	"github.com/labstack/echo/v5/middleware"
 	"go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp"
 	"go.opentelemetry.io/otel"
 	"go.opentelemetry.io/otel/attribute"
@@ -37,10 +37,12 @@ var (
 // ParseError parses an error and returns the corresponding HTTP status and
 // HTTP message.
 func ParseError(err error) (int, string) {
-	var echoErr *echo.HTTPError
-	ok := errors.As(err, &echoErr)
-	if ok {
-		return echoErr.Code, http.StatusText(echoErr.Code)
+	// [echo.StatusCode] also matches the router's ErrNotFound and
+	// ErrMethodNotAllowed sentinels, which Echo v5 no longer models as
+	// [echo.HTTPError]. Matching that type alone would let every unrouted
+	// request fall through to a 500.
+	if code := echo.StatusCode(err); code != 0 {
+		return code, http.StatusText(code)
 	}
 
 	if errors.Is(err, context.DeadlineExceeded) {
@@ -100,14 +102,14 @@ const statusClientClosedRequest = 499
 // A server-side timeout is [context.DeadlineExceeded], mapped to 503 by
 // [ParseError], and is deliberately not treated as a client abort.
 // See https://github.com/gotenberg/gotenberg/issues/1627.
-func requestCanceled(c echo.Context, err error) bool {
+func requestCanceled(c *echo.Context, err error) bool {
 	return errors.Is(err, context.Canceled) && errors.Is(c.Request().Context().Err(), context.Canceled)
 }
 
 // httpErrorHandler is the centralized HTTP error handler. It parses the error,
 // returns a response as "text/plain; charset=UTF-8".
 func httpErrorHandler() echo.HTTPErrorHandler {
-	return func(err error, c echo.Context) {
+	return func(c *echo.Context, err error) {
 		logger := c.Get("logger").(*slog.Logger)
 
 		if requestCanceled(c, err) {
@@ -134,7 +136,7 @@ func httpErrorHandler() echo.HTTPErrorHandler {
 //	startTime := c.Get("startTime").(time.Time)
 func latencyMiddleware() echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			// First piece for calculating the latency.
 			startTime := time.Now()
 			c.Set("startTime", startTime)
@@ -159,7 +161,7 @@ func latencyMiddleware() echo.MiddlewareFunc {
 //	}
 func rootPathMiddleware(rootPath string) echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			c.Set("rootPath", rootPath)
 			// Call the next middleware in the chain.
 			return next(c)
@@ -173,7 +175,7 @@ func rootPathMiddleware(rootPath string) echo.MiddlewareFunc {
 //	outputFilename := c.Get("outputFilename").(string)
 func outputFilenameMiddleware() echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			filename := c.Request().Header.Get("Gotenberg-Output-Filename")
 			// Keep only the last path segment, so that a caller cannot name an
 			// output file after a path.
@@ -203,10 +205,18 @@ func telemetryMiddleware(logger *slog.Logger, serverName, correlationIdHeader st
 	semconvSrv := semconvutil.NewHTTPServer(meter)
 
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			startTime := c.Get("startTime").(time.Time)
 			rootPath := c.Get("rootPath").(string)
 
+			// Echo v5 returns the bare [http.ResponseWriter] from
+			// Context.Response, so unwrap it to read the recorded status and
+			// size below.
+			response, errUnwrap := echo.UnwrapResponse(c.Response())
+			if errUnwrap != nil {
+				return fmt.Errorf("unwrap response: %w", errUnwrap)
+			}
+
 			request := c.Request()
 			savedCtx := request.Context()
 			defer func() {
@@ -239,7 +249,7 @@ func telemetryMiddleware(logger *slog.Logger, serverName, correlationIdHeader st
 
 				err := next(c)
 				if err != nil {
-					c.Error(err)
+					c.Echo().HTTPErrorHandler(c, err)
 				}
 				return nil
 			}
@@ -288,7 +298,7 @@ func telemetryMiddleware(logger *slog.Logger, serverName, correlationIdHeader st
 			err := next(c)
 			finishTime := time.Now()
 
-			status := c.Response().Status
+			status := response.Status
 			canceled := false
 			if err != nil {
 				canceled = requestCanceled(c, err)
@@ -300,58 +310,68 @@ func telemetryMiddleware(logger *slog.Logger, serverName, correlationIdHeader st
 				}
 
 				span.SetAttributes(attribute.String("error", err.Error()))
-				c.Error(err)
+				c.Echo().HTTPErrorHandler(c, err)
 			}
 
 			span.SetStatus(semconvSrv.Status(status))
 			span.SetAttributes(semconvSrv.ResponseTraceAttrs(semconvutil.ResponseTelemetry{
 				StatusCode: status,
-				WriteBytes: c.Response().Size,
+				WriteBytes: response.Size,
 			})...)
 
-			accessLogger := logger.
-				With(slog.String("log_type", "access")).
-				With(slog.String("correlation_id", correlationId)).
-				With(slog.String("remote_ip", c.RealIP())).
-				With(slog.String("host", c.Request().Host)).
-				With(slog.String("uri", c.Request().RequestURI)).
-				With(slog.String("method", c.Request().Method)).
-				With(slog.String("path", routePath)).
-				With(slog.String("referer", c.Request().Referer())).
-				With(slog.String("user_agent", c.Request().UserAgent())).
-				With(slog.Int("status", c.Response().Status)).
-				With(slog.Int64("latency", int64(finishTime.Sub(startTime)))).
-				With(slog.String("latency_human", finishTime.Sub(startTime).String())).
-				With(slog.Int64("bytes_in", c.Request().ContentLength)).
-				With(slog.Int64("bytes_out", c.Response().Size))
+			// Pick the level and message before building the record: err.Error
+			// walks a joined error chain, and the nil-error branch has no use
+			// for it.
+			level := slog.LevelInfo
+			msg := "request handled"
 
 			switch {
 			case err == nil:
-				accessLogger.InfoContext(ctx, "request handled")
 			case canceled:
 				// A client abort is expected, not a server failure; keep it
 				// visible but out of the error stream.
-				accessLogger.InfoContext(ctx, err.Error())
+				msg = err.Error()
 			default:
-				accessLogger.ErrorContext(ctx, err.Error())
+				level = slog.LevelError
+				msg = err.Error()
 			}
 
+			// One record rather than a chain of With calls. Each With clones
+			// the whole handler chain, and this logger fans out to a JSON
+			// handler and an OpenTelemetry bridge that is wired in even when no
+			// exporter is configured, so a 14-deep chain clones both sub-chains
+			// 14 times to emit a single line.
+			latency := finishTime.Sub(startTime)
+
+			logger.LogAttrs(ctx, level, msg,
+				slog.String("log_type", "access"),
+				slog.String("correlation_id", correlationId),
+				slog.String("remote_ip", c.RealIP()),
+				slog.String("host", c.Request().Host),
+				slog.String("uri", c.Request().RequestURI),
+				slog.String("method", c.Request().Method),
+				slog.String("path", routePath),
+				slog.String("referer", c.Request().Referer()),
+				slog.String("user_agent", c.Request().UserAgent()),
+				slog.Int("status", response.Status),
+				slog.Int64("latency", int64(latency)),
+				slog.String("latency_human", latency.String()),
+				slog.Int64("bytes_in", c.Request().ContentLength),
+				slog.Int64("bytes_out", response.Size),
+			)
+
 			additionalAttributes := []attribute.KeyValue{
 				semconvSrv.Route(routePath),
 			}
 
 			semconvSrv.RecordMetrics(ctx, semconvutil.ServerMetricData{
-				ServerName:   serverName,
-				ResponseSize: c.Response().Size,
-				MetricAttributes: semconvutil.MetricAttributes{
-					Req:                  request,
-					StatusCode:           status,
-					AdditionalAttributes: additionalAttributes,
-				},
-				MetricData: semconvutil.MetricData{
-					RequestSize: request.ContentLength,
-					ElapsedTime: float64(time.Since(startTime)) / float64(time.Millisecond),
-				},
+				ServerName:           serverName,
+				ResponseSize:         response.Size,
+				Req:                  request,
+				StatusCode:           status,
+				AdditionalAttributes: additionalAttributes,
+				RequestSize:          request.ContentLength,
+				ElapsedTime:          float64(time.Since(startTime)) / float64(time.Millisecond),
 			})
 
 			return nil
@@ -361,7 +381,7 @@ func telemetryMiddleware(logger *slog.Logger, serverName, correlationIdHeader st
 
 // basicAuthMiddleware manages basic authentication.
 func basicAuthMiddleware(username, password string) echo.MiddlewareFunc {
-	return middleware.BasicAuth(func(u string, p string, e echo.Context) (bool, error) {
+	return middleware.BasicAuth(func(c *echo.Context, u string, p string) (bool, error) {
 		if subtle.ConstantTimeCompare([]byte(u), []byte(username)) == 1 &&
 			subtle.ConstantTimeCompare([]byte(p), []byte(password)) == 1 {
 			return true, nil
@@ -407,7 +427,7 @@ func (a *Api) buildOidcVerifier() (*oidc.IDTokenVerifier, error) {
 // it to the client.
 func oidcAuthMiddleware(verifier *oidc.IDTokenVerifier) echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			rawToken, ok := strings.CutPrefix(c.Request().Header.Get("Authorization"), "Bearer ")
 			if !ok || rawToken == "" {
 				return echo.NewHTTPError(http.StatusUnauthorized, "a Bearer token is required in the Authorization header")
@@ -436,7 +456,7 @@ func oidcAuthMiddleware(verifier *oidc.IDTokenVerifier) echo.MiddlewareFunc {
 //	cancel := c.Get("cancel").(context.CancelFunc)
 func contextMiddleware(fs *gotenberg.FileSystem, timeout time.Duration, bodyLimit int64, downloadFromCfg downloadFromConfig) echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			logger, _ := c.Get("logger").(*slog.Logger)
 			if logger == nil {
 				return errors.New("no logger in context (possible pool reuse)")
@@ -497,7 +517,7 @@ func contextMiddleware(fs *gotenberg.FileSystem, timeout time.Duration, bodyLimi
 // handler fails to timeout as expected.
 func hardTimeoutMiddleware(hardTimeout time.Duration) echo.MiddlewareFunc {
 	return func(next echo.HandlerFunc) echo.HandlerFunc {
-		return func(c echo.Context) error {
+		return func(c *echo.Context) error {
 			// Guard the type assertion so a pooled [echo.Context] whose
 			// store has been recycled under us does not crash the process.
 			// See the webhook async handler for the race this protects

pkg/modules/api/middlewares_test.go

@@ -1,6 +1,7 @@
 package api
 
 import (
+	"bytes"
 	"context"
 	"crypto/rand"
 	"crypto/rsa"
@@ -9,13 +10,15 @@ import (
 	"log/slog"
 	"net/http"
 	"net/http/httptest"
+	"os"
+	"path/filepath"
 	"strings"
 	"testing"
 	"time"
 
 	"github.com/coreos/go-oidc/v3/oidc"
 	"github.com/coreos/go-oidc/v3/oidc/oidctest"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 )
 
 // TestRequestCanceled pins the client-abort discriminator: only a
@@ -73,7 +76,7 @@ func TestHttpErrorHandler_ClientClosedRequest(t *testing.T) {
 			c := echo.New().NewContext(req, rec)
 			c.Set("logger", slog.New(slog.DiscardHandler))
 
-			httpErrorHandler()(tc.err, c)
+			httpErrorHandler()(c, tc.err)
 
 			if rec.Code != tc.wantStatus {
 				t.Fatalf("status = %d, want %d", rec.Code, tc.wantStatus)
@@ -105,7 +108,7 @@ func TestOutputFilenameMiddleware(t *testing.T) {
 		{"control characters", "fo\x01o\x7f", "foo"},
 	} {
 		t.Run(tc.name, func(t *testing.T) {
-			handler := outputFilenameMiddleware()(func(c echo.Context) error { return nil })
+			handler := outputFilenameMiddleware()(func(c *echo.Context) error { return nil })
 
 			req := httptest.NewRequest(http.MethodPost, "/", nil)
 			if tc.header != "" {
@@ -131,7 +134,7 @@ func TestOutputFilenameMiddleware(t *testing.T) {
 
 func TestHardTimeoutMiddleware_MissingLoggerReturnsErrorInsteadOfPanicking(t *testing.T) {
 	mw := hardTimeoutMiddleware(100 * time.Millisecond)
-	handler := mw(func(c echo.Context) error { return nil })
+	handler := mw(func(c *echo.Context) error { return nil })
 
 	e := echo.New()
 	req := httptest.NewRequest(http.MethodGet, "/", nil)
@@ -220,7 +223,7 @@ func TestOidcAuthMiddleware(t *testing.T) {
 			}
 			c := echo.New().NewContext(req, httptest.NewRecorder())
 
-			handler := oidcAuthMiddleware(verifier)(func(c echo.Context) error {
+			handler := oidcAuthMiddleware(verifier)(func(c *echo.Context) error {
 				return c.NoContent(http.StatusOK)
 			})
 
@@ -243,3 +246,114 @@ func TestOidcAuthMiddleware(t *testing.T) {
 		})
 	}
 }
+
+// TestParseError_StatusMapping pins the statuses [ParseError] derives from the
+// errors Echo and Gotenberg produce.
+//
+// Echo v5 models the router's ErrNotFound and ErrMethodNotAllowed as an
+// unexported type rather than [echo.HTTPError], so matching that type alone
+// would turn every unrouted request into a 500. It also guards the ordering:
+// Gotenberg's own [SentinelHttpError] carries a client-facing message and must
+// not be shadowed by the generic status lookup.
+func TestParseError_StatusMapping(t *testing.T) {
+	for _, tc := range []struct {
+		scenario    string
+		err         error
+		wantStatus  int
+		wantMessage string
+	}{
+		{"router not found", echo.ErrNotFound, http.StatusNotFound, http.StatusText(http.StatusNotFound)},
+		{"router method not allowed", echo.ErrMethodNotAllowed, http.StatusMethodNotAllowed, http.StatusText(http.StatusMethodNotAllowed)},
+		{"explicit HTTP error", echo.NewHTTPError(http.StatusUnauthorized, "nope"), http.StatusUnauthorized, http.StatusText(http.StatusUnauthorized)},
+		{"wrapped HTTP error", fmt.Errorf("authenticate request: %w", echo.NewHTTPError(http.StatusUnauthorized, "nope")), http.StatusUnauthorized, http.StatusText(http.StatusUnauthorized)},
+		{"sentinel keeps its message", NewSentinelHttpError(http.StatusBadRequest, "Invalid 'foo' form field value"), http.StatusBadRequest, "Invalid 'foo' form field value"},
+		{"unknown error", errors.New("boom"), http.StatusInternalServerError, http.StatusText(http.StatusInternalServerError)},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			status, message := ParseError(tc.err)
+			if status != tc.wantStatus {
+				t.Fatalf("status = %d, want %d", status, tc.wantStatus)
+			}
+			if message != tc.wantMessage {
+				t.Fatalf("message = %q, want %q", message, tc.wantMessage)
+			}
+		})
+	}
+}
+
+// TestNewEchoServer_RealIP pins the client IP extraction that the access log's
+// "remote_ip" field depends on.
+//
+// Echo v5.1.0 dropped the X-Forwarded-For and X-Real-IP fallbacks from
+// Context.RealIP, so without an explicit extractor a Gotenberg behind a reverse
+// proxy would log the proxy's address for every request. [newEchoServer]
+// restores the previous behavior.
+func TestNewEchoServer_RealIP(t *testing.T) {
+	srv := newEchoServer()
+	if srv.IPExtractor == nil {
+		t.Fatal("no IPExtractor configured: remote_ip would report the proxy address")
+	}
+
+	for _, tc := range []struct {
+		scenario string
+		headers  map[string]string
+		want     string
+	}{
+		{"x-forwarded-for keeps the client, not the proxy", map[string]string{"X-Forwarded-For": "203.0.113.7, 70.41.3.18"}, "203.0.113.7"},
+		{"single x-forwarded-for", map[string]string{"X-Forwarded-For": "203.0.113.7"}, "203.0.113.7"},
+		{"bracketed IPv6 is unwrapped", map[string]string{"X-Forwarded-For": "[2001:db8::1], 70.41.3.18"}, "2001:db8::1"},
+		{"x-real-ip when no x-forwarded-for", map[string]string{"X-Real-IP": "203.0.113.9"}, "203.0.113.9"},
+		{"no headers falls back to the remote address", nil, "192.0.2.1"},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			req := httptest.NewRequest(http.MethodGet, "/", nil)
+			req.RemoteAddr = "192.0.2.1:1234"
+			for key, value := range tc.headers {
+				req.Header.Set(key, value)
+			}
+
+			c := srv.NewContext(req, httptest.NewRecorder())
+
+			if got := c.RealIP(); got != tc.want {
+				t.Fatalf("RealIP = %q, want %q", got, tc.want)
+			}
+		})
+	}
+}
+
+// TestNewEchoServer_AttachmentServesAbsolutePath pins the filesystem that every
+// conversion response is sent through.
+//
+// Echo v5 serves files through Echo.Filesystem, an [fs.FS] rooted at the working
+// directory, and [fs.FS] rejects absolute names. Gotenberg builds every output
+// file under the request's temporary directory and hands Context.Attachment an
+// absolute path, so with the default filesystem every conversion route answers
+// 404 while still reading the whole upload.
+func TestNewEchoServer_AttachmentServesAbsolutePath(t *testing.T) {
+	path := filepath.Join(t.TempDir(), "output.pdf")
+	want := []byte("%PDF-1.7 not really a PDF")
+
+	err := os.WriteFile(path, want, 0o600)
+	if err != nil {
+		t.Fatalf("write fixture: %v", err)
+	}
+
+	srv := newEchoServer()
+	rec := httptest.NewRecorder()
+	c := srv.NewContext(httptest.NewRequest(http.MethodPost, "/", nil), rec)
+
+	err = c.Attachment(path, "output.pdf")
+	if err != nil {
+		t.Fatalf("Attachment(%q) = %v, want nil", path, err)
+	}
+
+	if rec.Code != http.StatusOK {
+		t.Fatalf("status = %d, want %d", rec.Code, http.StatusOK)
+	}
+	if got := rec.Body.Bytes(); !bytes.Equal(got, want) {
+		t.Fatalf("body = %q, want %q", got, want)
+	}
+	if got := rec.Header().Get("Content-Disposition"); !strings.Contains(got, `filename="output.pdf"`) {
+		t.Fatalf("Content-Disposition = %q, want it to carry filename=\"output.pdf\"", got)
+	}
+}

pkg/modules/api/mocks.go

@@ -4,7 +4,7 @@ import (
 	"log/slog"
 
 	"github.com/alexliesenfeld/health"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
@@ -83,7 +83,7 @@ func (ctx *ContextMock) SetLogger(logger *slog.Logger) {
 //
 //	ctx := &api.ContextMock{Context: &api.Context{}}
 //	ctx.setEchoContext(c)
-func (ctx *ContextMock) SetEchoContext(c echo.Context) {
+func (ctx *ContextMock) SetEchoContext(c *echo.Context) {
 	ctx.echoCtx = c
 }
 

pkg/modules/chromium/browser.go

@@ -17,12 +17,31 @@ import (
 	"github.com/chromedp/cdproto/page"
 	"github.com/chromedp/cdproto/runtime"
 	"github.com/chromedp/chromedp"
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"github.com/shirou/gopsutil/v4/process"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
 
+// chromiumDisableFeatures is the value of Chromium's --disable-features
+// switch.
+//
+// It restates the "site-per-process,Translate,BlinkGenPropertyTrees" default
+// from chromedp.DefaultExecAllocatorOptions (chromedp v0.14.2) on purpose:
+// chromedp.Flag keys its flags by switch name, so a second --disable-features
+// replaces chromedp's value instead of merging with it. Revisit this list when
+// bumping chromedp.
+//
+// WebUIOmniboxPopup and WebUIOmniboxAimPopup became enabled by default in
+// Chromium 151.0.7922.132. Their presenters build the address-bar popup WebUI
+// at browser start, headless included, which leaves a renderer process holding
+// ~85 MB of anonymous memory for a UI a PDF service can never show. Chromium
+// silently ignores feature names it does not know, so both stay harmless on
+// older builds (they exist but default to disabled on the Chromium pinned for
+// ppc64el) and once upstream eventually removes them.
+// See https://github.com/gotenberg/gotenberg/issues/1656.
+const chromiumDisableFeatures = "site-per-process,Translate,BlinkGenPropertyTrees,WebUIOmniboxPopup,WebUIOmniboxAimPopup"
+
 type browser interface {
 	gotenberg.Process
 	pdf(ctx context.Context, logger *slog.Logger, url, outputPath string, options PdfOptions, aggregate *networkAggregate) error
@@ -133,6 +152,8 @@ func (b *chromiumBrowser) Start(logger *slog.Logger) error {
 		chromedp.Flag("disable-dev-shm-usage", true),
 		// See https://github.com/gotenberg/gotenberg/issues/1293.
 		chromedp.Flag("disable-component-update", false),
+		// See https://github.com/gotenberg/gotenberg/issues/1656.
+		chromedp.Flag("disable-features", chromiumDisableFeatures),
 	)
 
 	if b.arguments.allowInsecureLocalhost {
@@ -523,8 +544,45 @@ func (b *chromiumBrowser) do(ctx context.Context, logger *slog.Logger, url strin
 		cancelOnMainPageError:   taskCancel,
 	})
 
+	var (
+		crashed   error
+		crashedMu sync.RWMutex
+	)
+
+	// See https://github.com/gotenberg/gotenberg/issues/1640.
+	listenForEventTargetCrashed(taskCtx, logger, eventTargetCrashedOptions{
+		crashed:   &crashed,
+		crashedMu: &crashedMu,
+		cancel:    taskCancel,
+	})
+
 	runErr := chromedp.Run(taskCtx, tasks...)
 
+	// A crashed renderer is the root cause of every other failure this
+	// conversion may have recorded, so check it first.
+	// See https://github.com/gotenberg/gotenberg/issues/1640.
+	crashedMu.RLock()
+	defer crashedMu.RUnlock()
+
+	if crashed != nil {
+		return fmt.Errorf("handle tasks: %w", crashed)
+	}
+
+	// The browser context is only ever canceled when the browser process
+	// dies or is stopped, never on a request timeout. If the run failed
+	// and the browser context is done, the conversion failed because the
+	// browser went away mid-flight; fail fast with the same crash error
+	// instead of letting the error fall through as a generic context
+	// cancellation. The check is gated on runErr so a successful
+	// conversion is never discarded by a browser death that lands right
+	// after it.
+	// See https://github.com/gotenberg/gotenberg/issues/1640.
+	if runErr != nil {
+		if err := b.ctx.Err(); err != nil {
+			return fmt.Errorf("handle tasks: %w", ErrChromiumCrashed)
+		}
+	}
+
 	// Check event-driven errors first — they take priority over chromedp.Run
 	// errors because they carry the actual root cause (e.g., HTTP 500 from
 	// the main page). When we cancel taskCtx on a main page error,

pkg/modules/chromium/browser_test.go

@@ -3,6 +3,7 @@ package chromium
 import (
 	"context"
 	"log/slog"
+	"slices"
 	"strings"
 	"testing"
 )
@@ -37,3 +38,24 @@ func TestChromiumBrowser_Start_rejectsOverlappingStart(t *testing.T) {
 		t.Fatal("expected the browser to stay not started")
 	}
 }
+
+// TestChromiumDisableFeatures guards the override described in
+// https://github.com/gotenberg/gotenberg/issues/1656. Gotenberg replaces
+// chromedp's --disable-features value rather than extending it, as
+// chromedp.Flag keys its flags by switch name. Dropping one of chromedp's own
+// entries while editing this list would silently re-enable it.
+func TestChromiumDisableFeatures(t *testing.T) {
+	for _, feature := range []string{
+		// chromedp.DefaultExecAllocatorOptions.
+		"site-per-process",
+		"Translate",
+		"BlinkGenPropertyTrees",
+		// The address-bar popup WebUI, built even in headless.
+		"WebUIOmniboxPopup",
+		"WebUIOmniboxAimPopup",
+	} {
+		if !slices.Contains(strings.Split(chromiumDisableFeatures, ","), feature) {
+			t.Errorf("expected %q to be disabled, got %q", feature, chromiumDisableFeatures)
+		}
+	}
+}

pkg/modules/chromium/chromium.go

@@ -14,7 +14,7 @@ import (
 
 	"github.com/alexliesenfeld/health"
 	"github.com/chromedp/cdproto/network"
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	flag "github.com/spf13/pflag"
 	"go.opentelemetry.io/otel/attribute"
 	"go.opentelemetry.io/otel/codes"
@@ -71,6 +71,10 @@ var (
 	// ErrResourceLoadingFailed happens when one or more resources failed to load.
 	ErrResourceLoadingFailed = errors.New("resource loading failed")
 
+	// ErrChromiumCrashed happens when the Chromium renderer crashes during a
+	// conversion.
+	ErrChromiumCrashed = errors.New("chromium crashed")
+
 	// PDF specific.
 
 	// ErrOmitBackgroundWithoutPrintBackground happens if
@@ -471,7 +475,7 @@ func (mod *Chromium) Descriptor() gotenberg.ModuleDescriptor {
 			fs.String("chromium-host-resolver-rules", "", "Set custom mappings to the host resolver")
 			fs.String("chromium-proxy-server", "", "Set the outbound proxy server; this switch only affects HTTP and HTTPS requests")
 			fs.Bool("chromium-enable-environment-proxy", false, "Route Chromium's outbound requests through the proxy defined by the standard HTTP_PROXY, HTTPS_PROXY, and NO_PROXY variables, including credentials. Use this instead of --chromium-proxy-server for authenticated proxies, and leave --chromium-proxy-server and --chromium-host-resolver-rules unset")
-			fs.StringSlice("chromium-allow-list", []string{}, "Set the allowed URLs for Chromium using regular expressions - supports multiple values")
+			fs.StringSlice("chromium-allow-list", []string{}, `Set the allowed URLs for Chromium using regular expressions - supports multiple values. A match bypasses --chromium-deny-private-ips (CHROMIUM_DENY_PRIVATE_IPS) and --chromium-deny-public-ips (CHROMIUM_DENY_PUBLIC_IPS), so terminate the host or the pattern also matches suffix hosts, for example ^https?://internal\.svc(:|/|$)`)
 			fs.StringSlice("chromium-deny-list", []string{`^file:(?!//\/tmp/).*`}, "Set the denied URLs for Chromium using regular expressions - supports multiple values")
 			fs.Bool("chromium-deny-private-ips", false, "Reject URLs whose host resolves to a non-public IP address (loopback, RFC1918, link-local, unique-local). Enable on deployments that accept untrusted form input to mitigate SSRF against internal services")
 			fs.Bool("chromium-deny-public-ips", false, "Reject URLs whose host resolves to a public IP address. Enable on air-gapped or data-governed deployments to prevent outbound traffic from leaving a private network")
@@ -1106,6 +1110,8 @@ func chromiumErrorType(err error, queueReason string) string {
 		errors.Is(err, ErrInvalidEvaluationExpression),
 		errors.Is(err, ErrInvalidSelectorQuery):
 		return gotenberg.ErrorTypeInvalidInput
+	case errors.Is(err, ErrChromiumCrashed):
+		return "chromium_unavailable"
 	case errors.Is(err, gotenberg.ErrMaximumQueueSizeExceeded):
 		return queueReason
 	case errors.Is(err, gotenberg.ErrProcessAlreadyRestarting):

pkg/modules/chromium/errortype_test.go

@@ -21,6 +21,7 @@ func TestChromiumErrorType(t *testing.T) {
 		{"invalid resource http status", ErrInvalidResourceHttpStatusCode, "chromium_unavailable", "invalid_input"},
 		{"loading failed", ErrLoadingFailed, "chromium_unavailable", "invalid_input"},
 		{"resource loading failed", ErrResourceLoadingFailed, "chromium_unavailable", "invalid_input"},
+		{"crashed", ErrChromiumCrashed, "chromium_unavailable", "chromium_unavailable"},
 		{"invalid evaluation expression", ErrInvalidEvaluationExpression, "chromium_unavailable", "invalid_input"},
 		{"invalid selector query", ErrInvalidSelectorQuery, "chromium_unavailable", "invalid_input"},
 		{"pdf queue", gotenberg.ErrMaximumQueueSizeExceeded, "chromium_unavailable", "chromium_unavailable"},

pkg/modules/chromium/events.go

@@ -14,11 +14,12 @@ import (
 
 	"github.com/chromedp/cdproto/cdp"
 	"github.com/chromedp/cdproto/fetch"
+	"github.com/chromedp/cdproto/inspector"
 	"github.com/chromedp/cdproto/network"
 	"github.com/chromedp/cdproto/page"
 	"github.com/chromedp/cdproto/runtime"
 	"github.com/chromedp/chromedp"
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"golang.org/x/sync/errgroup"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
@@ -205,7 +206,7 @@ func listenForEventRequestPaused(ctx context.Context, logger *slog.Logger, optio
 						}
 
 						matchStart := time.Now()
-						ok, err := header.Scope.MatchString(e.Request.URL)
+						ok, err := gotenberg.MatchPattern(header.Scope, e.Request.URL)
 						budget.consume(time.Since(matchStart))
 
 						switch {
@@ -322,7 +323,15 @@ func listenForEventResponseReceived(
 				return
 			}
 
-			logger.DebugContext(ctx, fmt.Sprintf("event EventResponseReceived fired for a resource: %+v", ev.Response))
+			// Formatting the whole response is the most expensive thing this
+			// listener does, and it runs per sub-resource on chromedp's single
+			// per-target event goroutine while that goroutine holds the mutex
+			// it also takes to dispatch command responses. At the default log
+			// level the result is discarded, so gate it on the level rather
+			// than let slog drop it after the fact.
+			if logger.Enabled(ctx, slog.LevelDebug) {
+				logger.DebugContext(ctx, fmt.Sprintf("event EventResponseReceived fired for a resource: %+v", ev.Response))
+			}
 
 			if slices.Contains(options.failOnResourceOnHttpStatusCode, ev.Response.Status) {
 				if !shouldCheckResourceHttpStatusCode(ev.Response.URL, normalizedIgnoreDomains) {
@@ -521,6 +530,38 @@ func listenForEventExceptionThrown(ctx context.Context, logger *slog.Logger, con
 	})
 }
 
+type eventTargetCrashedOptions struct {
+	crashed   *error
+	crashedMu *sync.RWMutex
+	cancel    context.CancelFunc
+}
+
+// listenForEventTargetCrashed listens for the Inspector.targetCrashed event,
+// which Chromium sends when the renderer serving the conversion's tab
+// crashes. chromedp enables the Inspector domain on every target but does
+// not handle this event: left alone, the in-flight CDP command never
+// receives a response and the conversion blocks until the request deadline.
+// Record the crash and cancel the task context so the conversion fails fast
+// instead.
+// See https://github.com/gotenberg/gotenberg/issues/1640.
+func listenForEventTargetCrashed(ctx context.Context, logger *slog.Logger, options eventTargetCrashedOptions) {
+	chromedp.ListenTarget(ctx, func(ev any) {
+		if _, ok := ev.(*inspector.EventTargetCrashed); ok {
+			logger.DebugContext(ctx, "event EventTargetCrashed fired")
+
+			options.crashedMu.Lock()
+			defer options.crashedMu.Unlock()
+
+			*options.crashed = ErrChromiumCrashed
+
+			// Cancel the task context so the in-flight CDP command aborts
+			// immediately instead of waiting for a response the crashed
+			// renderer can never send.
+			options.cancel()
+		}
+	})
+}
+
 // waitForEventDomContentEventFired registers a listener for the
 // DomContentEventFired event and returns a waiter that blocks until the
 // event fires or ctx is done. The listener registers at call time, not

pkg/modules/chromium/network_aggregate.go

@@ -11,6 +11,15 @@ import (
 // pathological page cannot grow the set without limit.
 const maxTrackedOrigins = 64
 
+// maxTrackedRequests bounds the request id to URL map. Entries are dropped as
+// soon as the request settles, so the map normally holds only what is in
+// flight, but a request that never reports a loading-finished or
+// loading-failed event never settles. Without a cap, a page that opens
+// requests it never resolves would grow the map for the whole conversion, at
+// the cost of one full response URL per entry. Losing an entry only costs the
+// heaviest-resource URL attribution for that request.
+const maxTrackedRequests = 1024
+
 // networkAggregate accumulates per-conversion network activity from Chromium
 // DevTools events. It is safe for concurrent use by the chromedp event listener
 // goroutine and the conversion goroutine that reads the snapshot afterwards.
@@ -60,7 +69,9 @@ func (a *networkAggregate) onResponseReceived(ev *network.EventResponseReceived)
 			a.origins[origin] = struct{}{}
 		}
 	}
-	a.requestURLByID[ev.RequestID] = ev.Response.URL
+	if len(a.requestURLByID) < maxTrackedRequests {
+		a.requestURLByID[ev.RequestID] = ev.Response.URL
+	}
 }
 
 // onLoadingFinished records a successfully completed request and its size,
@@ -81,6 +92,11 @@ func (a *networkAggregate) onLoadingFinished(ev *network.EventLoadingFinished) {
 		a.heaviestBytes = size
 		a.heaviestURL = a.requestURLByID[ev.RequestID]
 	}
+
+	// The request has settled and nothing reads its URL again. Dropping it
+	// keeps the map proportional to the requests in flight rather than to
+	// every request the page ever made.
+	delete(a.requestURLByID, ev.RequestID)
 }
 
 // onLoadingFailed records a request that failed to complete.
@@ -94,6 +110,9 @@ func (a *networkAggregate) onLoadingFailed(ev *network.EventLoadingFailed) {
 
 	a.requestCount++
 	a.failedCount++
+
+	// Settled, like a finished request: its URL is never read again.
+	delete(a.requestURLByID, ev.RequestID)
 }
 
 func (a *networkAggregate) snapshot() networkStats {

pkg/modules/chromium/network_aggregate_test.go

@@ -98,3 +98,86 @@ func TestNetworkAggregate_ConcurrentSafe(t *testing.T) {
 		t.Errorf("requestCount = %d, want 100", got)
 	}
 }
+
+// TestNetworkAggregate_SettledRequestsAreDropped covers the growth where every
+// response URL stayed in the map for the whole conversion even though nothing
+// reads it again once the request settles.
+func TestNetworkAggregate_SettledRequestsAreDropped(t *testing.T) {
+	a := newNetworkAggregate()
+
+	for i := range 500 {
+		id := network.RequestID(fmt.Sprintf("r%d", i))
+		a.onResponseReceived(&network.EventResponseReceived{
+			RequestID: id,
+			Response:  &network.Response{URL: fmt.Sprintf("https://host.example.com/%d", i)},
+		})
+
+		if i%2 == 0 {
+			a.onLoadingFinished(&network.EventLoadingFinished{RequestID: id, EncodedDataLength: 10})
+			continue
+		}
+
+		a.onLoadingFailed(&network.EventLoadingFailed{RequestID: id})
+	}
+
+	a.mu.Lock()
+	tracked := len(a.requestURLByID)
+	a.mu.Unlock()
+
+	if tracked != 0 {
+		t.Errorf("tracked requests = %d, want 0: settled requests must not be retained", tracked)
+	}
+
+	// The bookkeeping the map feeds must survive the pruning.
+	got := a.snapshot()
+	if got.requestCount != 500 {
+		t.Errorf("requestCount = %d, want 500", got.requestCount)
+	}
+	if got.failedCount != 250 {
+		t.Errorf("failedCount = %d, want 250", got.failedCount)
+	}
+}
+
+// TestNetworkAggregate_UnsettledRequestCap verifies the ceiling that applies
+// when requests never settle, which is the only way the map can still grow.
+func TestNetworkAggregate_UnsettledRequestCap(t *testing.T) {
+	a := newNetworkAggregate()
+
+	for i := range maxTrackedRequests + 500 {
+		a.onResponseReceived(&network.EventResponseReceived{
+			RequestID: network.RequestID(fmt.Sprintf("r%d", i)),
+			Response:  &network.Response{URL: fmt.Sprintf("https://host.example.com/%d", i)},
+		})
+	}
+
+	a.mu.Lock()
+	tracked := len(a.requestURLByID)
+	a.mu.Unlock()
+
+	if tracked != maxTrackedRequests {
+		t.Errorf("tracked requests = %d, want %d (capped)", tracked, maxTrackedRequests)
+	}
+}
+
+// TestNetworkAggregate_HeaviestURLSurvivesPruning guards the attribution the
+// map exists for: the URL must still be resolved before the entry is dropped.
+func TestNetworkAggregate_HeaviestURLSurvivesPruning(t *testing.T) {
+	a := newNetworkAggregate()
+
+	a.onResponseReceived(&network.EventResponseReceived{
+		RequestID: "small",
+		Response:  &network.Response{URL: "https://example.com/small.css"},
+	})
+	a.onLoadingFinished(&network.EventLoadingFinished{RequestID: "small", EncodedDataLength: 10})
+
+	a.onResponseReceived(&network.EventResponseReceived{
+		RequestID: "big",
+		Response:  &network.Response{URL: "https://example.com/big.png"},
+	})
+	a.onLoadingFinished(&network.EventLoadingFinished{RequestID: "big", EncodedDataLength: 4096})
+
+	got := a.snapshot()
+	if got.heaviestURL != "https://example.com/big.png" || got.heaviestBytes != 4096 {
+		t.Errorf("heaviest = (%q, %d), want (%q, 4096)", got.heaviestURL, got.heaviestBytes, "https://example.com/big.png")
+	}
+}

pkg/modules/chromium/pinning_proxy.go

@@ -11,9 +11,10 @@ import (
 	"net/netip"
 	"net/url"
 	"sync"
+	"sync/atomic"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"golang.org/x/net/http/httpproxy"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
@@ -57,6 +58,18 @@ type pinningProxy struct {
 	server   *http.Server
 	wg       sync.WaitGroup
 
+	// closing is closed by Stop to force in-flight CONNECT tunnels shut.
+	// [http.Server.Shutdown] cannot do it: net/http untracks a connection once
+	// a handler hijacks it, so a tunnel would otherwise outlive the proxy that
+	// created it. Recreated on every Start.
+	closing chan struct{}
+
+	// maxTunnels ceilings the CONNECT handlers in flight. Tests may lower it.
+	maxTunnels int64
+
+	// tunnels counts the CONNECT handlers in flight.
+	tunnels atomic.Int64
+
 	logger  *slog.Logger
 	started bool
 	mu      sync.Mutex
@@ -82,6 +95,7 @@ func newPinningProxy(allowList, denyList []*regexp2.Regexp, denyPrivateIPs, deny
 			dialer := &net.Dialer{Timeout: 10 * time.Second}
 			return dialer.DialContext(ctx, network, addr)
 		},
+		maxTunnels: maxConcurrentTunnels,
 	}
 
 	if enableEnvironmentProxy {
@@ -110,6 +124,7 @@ func (p *pinningProxy) Start(logger *slog.Logger) error {
 	}
 
 	p.listener = l
+	p.closing = make(chan struct{})
 	p.logger = logger.With(slog.String("logger", "pinning-proxy"))
 	p.server = &http.Server{
 		Handler: http.HandlerFunc(p.serveHTTP),
@@ -140,9 +155,18 @@ func (p *pinningProxy) Stop(logger *slog.Logger) error {
 		return nil
 	}
 	srv := p.server
+	closing := p.closing
+	p.closing = nil
 	p.started = false
 	p.mu.Unlock()
 
+	// Force in-flight tunnels shut before draining the server. Shutdown does
+	// not reach them, so a tunnel whose upstream never answers would otherwise
+	// survive the proxy, and with it every Chromium restart.
+	if closing != nil {
+		close(closing)
+	}
+
 	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
 	defer cancel()
 
@@ -181,6 +205,25 @@ func (p *pinningProxy) serveHTTP(w http.ResponseWriter, req *http.Request) {
 // Chromium then negotiates TLS end-to-end with the original hostname in
 // SNI.
 func (p *pinningProxy) handleConnect(w http.ResponseWriter, req *http.Request) {
+	// A ceiling, not a tuning knob: it bounds what a tunnel that refuses to end
+	// can accumulate, whatever keeps it alive. [spliceIdleTimeout] ends a silent
+	// tunnel, but a peer trickling a byte just under it stays "active" forever,
+	// and a compromised renderer can hold the client side open to match.
+	//
+	// Chromium caps itself well below this. Its socket pool manager allows 128
+	// sockets per proxy chain for normal traffic plus 128 for WebSocket
+	// traffic, and every request Gotenberg's Chromium makes traverses this one
+	// proxy chain, so an honest browser cannot exceed 256 tunnels here. At
+	// double that, a real page never meets the ceiling and a hostile one stops
+	// at it.
+	if !p.acquireTunnel() {
+		p.logger.WarnContext(req.Context(), fmt.Sprintf("CONNECT to '%s' refused: %d tunnels already in flight", req.Host, p.maxTunnels))
+		http.Error(w, "too many tunnels", http.StatusServiceUnavailable)
+
+		return
+	}
+	defer p.releaseTunnel()
+
 	_, port, err := net.SplitHostPort(req.Host)
 	if err != nil {
 		http.Error(w, "bad CONNECT target", http.StatusBadRequest)
@@ -264,24 +307,142 @@ func (p *pinningProxy) handleConnect(w http.ResponseWriter, req *http.Request) {
 		return
 	}
 
-	// Splice bytes in both directions until either side closes.
-	var splice sync.WaitGroup
-	splice.Add(2)
+	p.mu.Lock()
+	closing := p.closing
+	p.mu.Unlock()
+
+	spliceTunnel(client, upstream, closing, spliceIdleTimeout)
+}
+
+// maxConcurrentTunnels is the default for [pinningProxy.maxTunnels]. See
+// [pinningProxy.handleConnect] for how the value is derived.
+const maxConcurrentTunnels = 512
+
+// acquireTunnel reserves a slot for one CONNECT handler, reporting false when
+// the proxy is already at [pinningProxy.maxTunnels]. The compare-and-swap loop
+// keeps the check and the increment atomic, so concurrent handlers cannot
+// overshoot the ceiling between them.
+func (p *pinningProxy) acquireTunnel() bool {
+	for {
+		current := p.tunnels.Load()
+		if current >= p.maxTunnels {
+			return false
+		}
+		if p.tunnels.CompareAndSwap(current, current+1) {
+			return true
+		}
+	}
+}
+
+// releaseTunnel returns a slot taken by [pinningProxy.acquireTunnel].
+func (p *pinningProxy) releaseTunnel() {
+	p.tunnels.Add(-1)
+}
+
+// spliceIdleTimeout bounds a CONNECT tunnel in which no byte has moved in
+// either direction.
+//
+// Nothing else bounds one. The hijacked connections carry no deadline: the
+// server clears the header read deadline once the request line is in, and
+// net.Dialer.Timeout only covers the connect. net/http also untracks a
+// connection once it is hijacked, so neither Server.Shutdown nor a Chromium
+// restart reaps it. Left alone, an upstream that accepts the tunnel and then
+// answers nothing holds two goroutines and two sockets until the process dies.
+//
+// Sized well above any legitimate pause between a request and its response, so
+// a slow origin is never cut off. A transfer that keeps making progress
+// refreshes the deadline and runs for as long as it needs.
+const spliceIdleTimeout = 2 * time.Minute
+
+// spliceTunnel copies bytes between the two ends of a CONNECT tunnel until
+// both directions finish, the tunnel sits idle for idleTimeout, or closing is
+// closed because the proxy is shutting down. Callers pass
+// [spliceIdleTimeout]; only tests shorten it.
+//
+// Each direction half-closes its destination once its source reaches EOF, so a
+// peer that waits for the request to end before answering still sees the EOF.
+// Idleness is tracked across both directions rather than per direction: the
+// client sends nothing for the length of a download, and half-closing its write
+// side then would tell the origin the client had gone away.
+func spliceTunnel(client, upstream net.Conn, closing <-chan struct{}, idleTimeout time.Duration) {
+	var lastActivity atomic.Int64
+	lastActivity.Store(time.Now().UnixNano())
+
+	var wg sync.WaitGroup
+	wg.Add(2)
 	go func() {
-		defer splice.Done()
-		_, _ = io.Copy(upstream, client)
+		defer wg.Done()
+		copyTracking(upstream, client, &lastActivity, idleTimeout)
 		if cw, ok := upstream.(interface{ CloseWrite() error }); ok {
 			_ = cw.CloseWrite()
 		}
 	}()
 	go func() {
-		defer splice.Done()
-		_, _ = io.Copy(client, upstream)
+		defer wg.Done()
+		copyTracking(client, upstream, &lastActivity, idleTimeout)
 		if cw, ok := client.(interface{ CloseWrite() error }); ok {
 			_ = cw.CloseWrite()
 		}
 	}()
-	splice.Wait()
+
+	done := make(chan struct{})
+	go func() {
+		wg.Wait()
+		close(done)
+	}()
+
+	ticker := time.NewTicker(idleTimeout / 4)
+	defer ticker.Stop()
+
+	for {
+		select {
+		case <-done:
+			return
+		case <-closing:
+		case <-ticker.C:
+			if time.Since(time.Unix(0, lastActivity.Load())) < idleTimeout {
+				continue
+			}
+		}
+
+		// Closing both ends unblocks whichever copy is still reading. The
+		// caller's own deferred Close calls then become no-ops.
+		_ = client.Close()
+		_ = upstream.Close()
+		<-done
+
+		return
+	}
+}
+
+// copyTracking copies src into dst, recording the time of every chunk that
+// moves so [spliceTunnel] can tell a busy tunnel from an idle one.
+func copyTracking(dst, src net.Conn, lastActivity *atomic.Int64, writeTimeout time.Duration) {
+	buf := make([]byte, 32*1024)
+
+	for {
+		n, readErr := src.Read(buf)
+		if n > 0 {
+			lastActivity.Store(time.Now().UnixNano())
+
+			// Bound the write. A destination that has gone away accepts the
+			// first chunk into its send buffer and only fails on the next one,
+			// so without a deadline this direction keeps a dead tunnel alive
+			// for one more chunk. A destination that stops reading altogether
+			// would block here forever.
+			_ = dst.SetWriteDeadline(time.Now().Add(writeTimeout))
+
+			_, writeErr := dst.Write(buf[:n])
+			if writeErr != nil {
+				return
+			}
+
+			lastActivity.Store(time.Now().UnixNano())
+		}
+		if readErr != nil {
+			return
+		}
+	}
 }
 
 // handleForward handles plain HTTP requests sent to the proxy as absolute

pkg/modules/chromium/pinning_proxy_test.go

@@ -18,7 +18,7 @@ import (
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
@@ -898,3 +898,280 @@ func TestPinningProxy_StopIdempotent(t *testing.T) {
 		t.Fatalf("second Stop on stopped proxy: %v", err)
 	}
 }
+
+// tcpPair returns the two ends of a connected loopback TCP connection. Both
+// ends are closed when the test finishes.
+func tcpPair(t *testing.T) (net.Conn, net.Conn) {
+	t.Helper()
+
+	listener, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("listen: %v", err)
+	}
+	defer func() { _ = listener.Close() }()
+
+	type accepted struct {
+		conn net.Conn
+		err  error
+	}
+
+	acceptChan := make(chan accepted, 1)
+	go func() {
+		conn, acceptErr := listener.Accept()
+		acceptChan <- accepted{conn: conn, err: acceptErr}
+	}()
+
+	dialed, err := net.Dial("tcp", listener.Addr().String())
+	if err != nil {
+		t.Fatalf("dial: %v", err)
+	}
+
+	res := <-acceptChan
+	if res.err != nil {
+		t.Fatalf("accept: %v", res.err)
+	}
+
+	t.Cleanup(func() {
+		_ = dialed.Close()
+		_ = res.conn.Close()
+	})
+
+	return dialed, res.conn
+}
+
+// TestSpliceTunnel_IdleTunnelIsClosed covers the leak where an upstream that
+// accepted a CONNECT tunnel and then never spoke pinned both splice goroutines
+// and both sockets for the lifetime of the process. A hijacked connection
+// carries no deadline and net/http stops tracking it, so the idle bound in
+// spliceTunnel is the only thing that ends such a tunnel.
+func TestSpliceTunnel_IdleTunnelIsClosed(t *testing.T) {
+	// The peers are kept open by the pair's cleanup: the tunnel is silent, not
+	// finished.
+	client, _ := tcpPair(t)
+	upstream, _ := tcpPair(t)
+
+	done := make(chan struct{})
+	go func() {
+		spliceTunnel(client, upstream, nil, 100*time.Millisecond)
+		close(done)
+	}()
+
+	select {
+	case <-done:
+	case <-time.After(10 * time.Second):
+		t.Fatal("spliceTunnel did not return on an idle tunnel")
+	}
+}
+
+// TestSpliceTunnel_ClosingShutsTunnelDown verifies that stopping the proxy
+// reaps in-flight tunnels. http.Server.Shutdown cannot: it stops tracking a
+// connection once a handler hijacks it, so without this signal a tunnel would
+// outlive the proxy and every Chromium restart after it.
+func TestSpliceTunnel_ClosingShutsTunnelDown(t *testing.T) {
+	client, _ := tcpPair(t)
+	upstream, _ := tcpPair(t)
+
+	closing := make(chan struct{})
+	done := make(chan struct{})
+
+	go func() {
+		// An idle timeout far beyond the test: only closing can end this.
+		spliceTunnel(client, upstream, closing, time.Hour)
+		close(done)
+	}()
+
+	close(closing)
+
+	select {
+	case <-done:
+	case <-time.After(10 * time.Second):
+		t.Fatal("spliceTunnel did not return when the proxy shut down")
+	}
+}
+
+// TestSpliceTunnel_ActiveTransferOutlivesIdleTimeout guards the idle bound
+// against cutting a healthy transfer. Idleness is tracked across both
+// directions, so a download that keeps making progress must survive well past
+// the timeout even though the client sends nothing throughout.
+func TestSpliceTunnel_ActiveTransferOutlivesIdleTimeout(t *testing.T) {
+	const (
+		idleTimeout = 100 * time.Millisecond
+		chunks      = 10
+		interval    = 30 * time.Millisecond
+	)
+
+	client, clientPeer := tcpPair(t)
+	upstream, upstreamPeer := tcpPair(t)
+
+	done := make(chan struct{})
+	go func() {
+		spliceTunnel(client, upstream, nil, idleTimeout)
+		close(done)
+	}()
+
+	// Trickle a response for well over the idle timeout, then finish.
+	go func() {
+		for range chunks {
+			_, _ = upstreamPeer.Write([]byte("x"))
+			time.Sleep(interval)
+		}
+		_ = upstreamPeer.Close()
+	}()
+
+	received := 0
+	buf := make([]byte, chunks)
+
+	for received < chunks {
+		err := clientPeer.SetReadDeadline(time.Now().Add(10 * time.Second))
+		if err != nil {
+			t.Fatalf("set read deadline: %v", err)
+		}
+
+		n, readErr := clientPeer.Read(buf)
+		received += n
+		if readErr != nil {
+			break
+		}
+	}
+
+	if received != chunks {
+		t.Fatalf("received %d bytes, want %d: the tunnel was cut while still transferring", received, chunks)
+	}
+
+	select {
+	case <-done:
+	case <-time.After(10 * time.Second):
+		t.Fatal("spliceTunnel did not return after the upstream closed")
+	}
+}
+
+// TestPinningProxy_CONNECT_TunnelCeiling verifies the ceiling that bounds what
+// tunnels refusing to end can accumulate. The idle bound cannot cover a peer
+// that trickles just under it, so the count is what stops the growth.
+func TestPinningProxy_CONNECT_TunnelCeiling(t *testing.T) {
+	// An upstream that accepts and then says nothing: the tunnel stays open.
+	upstreamAddr, stop := newRawTCPServer(t, func(c net.Conn) {
+		<-make(chan struct{})
+	})
+	t.Cleanup(stop)
+
+	p := newPinningProxy(nil, nil, false, false, false)
+	p.maxTunnels = 1
+	p.decide = func(_ context.Context, _ string, _, _ []*regexp2.Regexp, _ time.Time) (gotenberg.OutboundDecision, error) {
+		return gotenberg.OutboundDecision{Pinned: []netip.Addr{netip.MustParseAddr("127.0.0.1")}}, nil
+	}
+	p.dialPinned = func(_ context.Context, network string, _ []netip.Addr, _ string) (net.Conn, error) {
+		return net.Dial(network, upstreamAddr)
+	}
+	proxyURL := newProxyForTest(t, p)
+	proxyAddr := strings.TrimPrefix(proxyURL, "http://")
+
+	connect := func(t *testing.T) *bufio.Reader {
+		t.Helper()
+
+		conn, err := net.Dial("tcp", proxyAddr)
+		if err != nil {
+			t.Fatalf("dial proxy: %v", err)
+		}
+		t.Cleanup(func() { _ = conn.Close() })
+
+		err = conn.SetDeadline(time.Now().Add(10 * time.Second))
+		if err != nil {
+			t.Fatalf("set deadline: %v", err)
+		}
+
+		_, err = fmt.Fprintf(conn, "CONNECT example.com:443 HTTP/1.1\r\nHost: example.com:443\r\n\r\n")
+		if err != nil {
+			t.Fatalf("write CONNECT: %v", err)
+		}
+
+		return bufio.NewReader(conn)
+	}
+
+	first := connect(t)
+	statusLine, err := first.ReadString('\n')
+	if err != nil {
+		t.Fatalf("read first status: %v", err)
+	}
+	if !strings.Contains(statusLine, " 200 ") {
+		t.Fatalf("first CONNECT status = %q, want 200", statusLine)
+	}
+
+	// The first tunnel now holds the only slot.
+	second := connect(t)
+	resp, err := http.ReadResponse(second, nil)
+	if err != nil {
+		t.Fatalf("read second response: %v", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	if resp.StatusCode != http.StatusServiceUnavailable {
+		t.Fatalf("second CONNECT status = %d, want %d", resp.StatusCode, http.StatusServiceUnavailable)
+	}
+
+	if got := p.tunnels.Load(); got != 1 {
+		t.Errorf("tunnels in flight = %d, want 1: a refused CONNECT must not consume a slot", got)
+	}
+}
+
+// TestPinningProxy_TunnelSlotIsReleased verifies a completed tunnel gives its
+// slot back, so the ceiling bounds concurrency rather than lifetime totals.
+func TestPinningProxy_TunnelSlotIsReleased(t *testing.T) {
+	upstreamAddr, stop := newRawTCPServer(t, func(c net.Conn) {
+		defer c.Close()
+		_, _ = c.Write([]byte("HI"))
+	})
+	t.Cleanup(stop)
+
+	p := newPinningProxy(nil, nil, false, false, false)
+	p.maxTunnels = 1
+	p.decide = func(_ context.Context, _ string, _, _ []*regexp2.Regexp, _ time.Time) (gotenberg.OutboundDecision, error) {
+		return gotenberg.OutboundDecision{Pinned: []netip.Addr{netip.MustParseAddr("127.0.0.1")}}, nil
+	}
+	p.dialPinned = func(_ context.Context, network string, _ []netip.Addr, _ string) (net.Conn, error) {
+		return net.Dial(network, upstreamAddr)
+	}
+	proxyURL := newProxyForTest(t, p)
+	proxyAddr := strings.TrimPrefix(proxyURL, "http://")
+
+	for attempt := range 3 {
+		conn, err := net.Dial("tcp", proxyAddr)
+		if err != nil {
+			t.Fatalf("attempt %d dial proxy: %v", attempt, err)
+		}
+
+		err = conn.SetDeadline(time.Now().Add(10 * time.Second))
+		if err != nil {
+			t.Fatalf("attempt %d set deadline: %v", attempt, err)
+		}
+
+		_, err = fmt.Fprintf(conn, "CONNECT example.com:443 HTTP/1.1\r\nHost: example.com:443\r\n\r\n")
+		if err != nil {
+			t.Fatalf("attempt %d write CONNECT: %v", attempt, err)
+		}
+
+		br := bufio.NewReader(conn)
+		statusLine, err := br.ReadString('\n')
+		if err != nil {
+			t.Fatalf("attempt %d read status: %v", attempt, err)
+		}
+		if !strings.Contains(statusLine, " 200 ") {
+			t.Fatalf("attempt %d CONNECT status = %q, want 200: the slot was not released", attempt, statusLine)
+		}
+
+		// Drain until the upstream's close ends the tunnel, then release it.
+		_, _ = io.ReadAll(br)
+		_ = conn.Close()
+
+		// The handler returns just after the splice ends.
+		for range 100 {
+			if p.tunnels.Load() == 0 {
+				break
+			}
+			time.Sleep(20 * time.Millisecond)
+		}
+		if got := p.tunnels.Load(); got != 0 {
+			t.Fatalf("attempt %d: tunnels in flight = %d, want 0", attempt, got)
+		}
+	}
+}

pkg/modules/chromium/pinning_proxy_upstream_test.go

@@ -14,7 +14,7 @@ import (
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )

pkg/modules/chromium/routes.go

@@ -14,9 +14,9 @@ import (
 	"strings"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"github.com/gomarkdown/markdown"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 	"github.com/microcosm-cc/bluemonday"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
@@ -466,7 +466,7 @@ func convertUrlRoute(chromium Api, engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/convert/url",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumPdfOptions(ctx)
 			mode := pdfengines.FormDataPdfSplitMode(form, false)
@@ -528,7 +528,7 @@ func screenshotUrlRoute(chromium Api) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/screenshot/url",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumScreenshotOptions(ctx)
 
@@ -562,7 +562,7 @@ func convertHtmlRoute(chromium Api, engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/convert/html",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumPdfOptions(ctx)
 			mode := pdfengines.FormDataPdfSplitMode(form, false)
@@ -621,7 +621,7 @@ func screenshotHtmlRoute(chromium Api) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/screenshot/html",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumScreenshotOptions(ctx)
 
@@ -652,7 +652,7 @@ func convertMarkdownRoute(chromium Api, engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/convert/markdown",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumPdfOptions(ctx)
 			mode := pdfengines.FormDataPdfSplitMode(form, false)
@@ -720,7 +720,7 @@ func screenshotMarkdownRoute(chromium Api) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/chromium/screenshot/markdown",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			form, options := FormDataChromiumScreenshotOptions(ctx)
 
@@ -1020,6 +1020,16 @@ func handleChromiumError(err error, options Options) error {
 		return nil
 	}
 
+	if errors.Is(err, ErrChromiumCrashed) {
+		return api.WrapError(
+			err,
+			api.NewSentinelHttpError(
+				http.StatusServiceUnavailable,
+				"Chromium crashed while processing the request. Retry, or reduce the workload if the problem persists.",
+			),
+		)
+	}
+
 	if errors.Is(err, ErrInvalidEvaluationExpression) {
 		if options.WaitForExpression == "" {
 			// We do not expect the 'waitWindowStatus' form field to return

pkg/modules/chromium/routes_test.go

@@ -0,0 +1,51 @@
+package chromium
+
+import (
+	"fmt"
+	"net/http"
+	"testing"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
+)
+
+// TestHandleChromiumError_Crashed pins the mapping of a Chromium renderer
+// crash to a 503 Service Unavailable. When the renderer crashes mid-conversion,
+// the request must fail fast with 503 rather than hang until the deadline and
+// surface as a generic timeout.
+// See https://github.com/gotenberg/gotenberg/issues/1640.
+func TestHandleChromiumError_Crashed(t *testing.T) {
+	// Mirror the wrapping done by [chromiumBrowser.do].
+	err := handleChromiumError(fmt.Errorf("handle tasks: %w", ErrChromiumCrashed), Options{})
+	if err == nil {
+		t.Fatal("expected an error, got none")
+	}
+
+	status, message := api.ParseError(err)
+	if status != http.StatusServiceUnavailable {
+		t.Errorf("status = %d, want %d (message: %s)", status, http.StatusServiceUnavailable, message)
+	}
+
+	want := "Chromium crashed while processing the request. Retry, or reduce the workload if the problem persists."
+	if message != want {
+		t.Errorf("message = %q, want %q", message, want)
+	}
+}
+
+// TestHandleChromiumError_CrashedTakesPrecedence guards the ordering in
+// [handleChromiumError]: a crash is a server-side failure and must map to 503
+// even when the error chain also carries a marker that another branch would
+// map to a client-error status.
+func TestHandleChromiumError_CrashedTakesPrecedence(t *testing.T) {
+	err := handleChromiumError(
+		fmt.Errorf("handle tasks: %w; %w", ErrChromiumCrashed, ErrInvalidHttpStatusCode),
+		Options{},
+	)
+	if err == nil {
+		t.Fatal("expected an error, got none")
+	}
+
+	status, _ := api.ParseError(err)
+	if status != http.StatusServiceUnavailable {
+		t.Errorf("status = %d, want %d", status, http.StatusServiceUnavailable)
+	}
+}

pkg/modules/chromium/scopebudget_test.go

@@ -6,7 +6,9 @@ import (
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
 
 func TestScopeMatchBudget(t *testing.T) {
@@ -90,7 +92,7 @@ func TestScopeMatchBudget_BoundsCatastrophicBacktracking(t *testing.T) {
 			break
 		}
 		matchStart := time.Now()
-		_, _ = pattern.MatchString(url)
+		_, _ = gotenberg.MatchPattern(pattern, url)
 		b.consume(time.Since(matchStart))
 		matched++
 	}
@@ -100,10 +102,13 @@ func TestScopeMatchBudget_BoundsCatastrophicBacktracking(t *testing.T) {
 		t.Errorf("all %d headers were matched, want the budget to stop matching early", headers)
 	}
 
-	// Each match is separately capped at extraHttpHeaderScopeMatchTimeout, so
-	// the worst case is the budget plus one final match that started with the
-	// last of the credit. Generous slack keeps this stable on a loaded CI box.
-	ceiling := budget + extraHttpHeaderScopeMatchTimeout + time.Second
+	// A match that is genuinely out of budget costs a few
+	// extraHttpHeaderScopeMatchTimeout rather than one:
+	// [gotenberg.MatchPattern] retries an abort to tell a real runaway from
+	// one caused by the process losing the CPU. The worst case is the budget
+	// plus one final match that started with the last of the credit. Generous
+	// slack keeps this stable on a loaded CI box.
+	ceiling := budget + 4*extraHttpHeaderScopeMatchTimeout + time.Second
 	if elapsed > ceiling {
 		t.Errorf("matching took %s, want at most %s", elapsed, ceiling)
 	}

pkg/modules/exiftool/exiftool.go

@@ -80,6 +80,37 @@ var dangerousTags = []string{
 	"FilePermissions", // Writing this changes the file's permissions
 }
 
+// controlOptions lists ExifTool command-line option names that collide with a
+// tag assignment. A metadata key of "csv" becomes the argv entry "-csv=value",
+// which exiftool reads as its own option rather than as a tag, so the value
+// becomes a filename exiftool opens. Only an unprefixed key can collide:
+// "-XMP:csv=value" is unambiguously a tag.
+//
+// See https://exiftool.org/exiftool_pod.html.
+var controlOptions = []string{
+	"api", "argfile", "charset", "common_args", "config", "csv", "diff",
+	"echo", "efile", "execute", "ext", "fileorder", "geotag", "geosync",
+	"htmldump", "if", "json", "lang", "listitem", "o", "out", "p", "php",
+	"require", "srcfile", "stay_open", "tagsfromfile", "textout", "use", "w",
+	"wm", "xmlformat",
+}
+
+// isControlOption reports whether an unprefixed key would reach exiftool as
+// one of its own options instead of as a tag assignment.
+func isControlOption(key string) bool {
+	if strings.Contains(key, ":") {
+		return false
+	}
+
+	for _, option := range controlOptions {
+		if strings.EqualFold(key, option) {
+			return true
+		}
+	}
+
+	return false
+}
+
 // isDangerousTag reports whether key matches one of the [dangerousTags]
 // after case-insensitive comparison with any group prefix stripped.
 func isDangerousTag(key string) bool {
@@ -114,6 +145,9 @@ func buildExifToolWriteArgs(metadata map[string]any) ([]string, error) {
 		if !safeKeyPattern.MatchString(key) {
 			return nil, fmt.Errorf("write PDF metadata with ExifTool: invalid metadata key %q: %w", key, gotenberg.ErrPdfEngineMetadataValueNotSupported)
 		}
+		if isControlOption(key) {
+			return nil, fmt.Errorf("write PDF metadata with ExifTool: metadata key %q is an ExifTool option, prefix it with a group such as %q: %w", key, "XMP:"+key, gotenberg.ErrPdfEngineMetadataValueNotSupported)
+		}
 
 		tag := key
 		if key == "Trapped" {

pkg/modules/exiftool/exiftool_test.go

@@ -2,6 +2,7 @@ package exiftool
 
 import (
 	"errors"
+	"fmt"
 	"slices"
 	"testing"
 
@@ -211,3 +212,48 @@ func TestSafeKeyPattern(t *testing.T) {
 		}
 	}
 }
+
+// A metadata key that collides with an ExifTool option becomes a bare argv
+// entry such as "-csv=/etc/passwd", which exiftool reads as its own option and
+// treats the value as a filename to open.
+func TestBuildExifToolWriteArgs_RejectsControlOptions(t *testing.T) {
+	for _, key := range []string{"csv", "CSV", "json", "geotag", "config", "tagsFromFile", "execute", "stay_open", "o", "w", "if", "p"} {
+		t.Run(key, func(t *testing.T) {
+			_, err := buildExifToolWriteArgs(map[string]any{key: "/etc/passwd"})
+			if err == nil {
+				t.Fatalf("buildExifToolWriteArgs accepted the control option %q", key)
+			}
+			if !errors.Is(err, gotenberg.ErrPdfEngineMetadataValueNotSupported) {
+				t.Fatalf("error %v does not wrap ErrPdfEngineMetadataValueNotSupported", err)
+			}
+		})
+	}
+}
+
+// A group prefix makes the key unambiguous, so it must still be accepted.
+func TestBuildExifToolWriteArgs_AcceptsPrefixedOptionNames(t *testing.T) {
+	for _, key := range []string{"XMP:csv", "XMP-dc:json", "IPTC:p"} {
+		t.Run(key, func(t *testing.T) {
+			args, err := buildExifToolWriteArgs(map[string]any{key: "value"})
+			if err != nil {
+				t.Fatalf("buildExifToolWriteArgs rejected the prefixed key %q: %v", key, err)
+			}
+			want := fmt.Sprintf("-%s=value", key)
+			if len(args) != 1 || args[0] != want {
+				t.Fatalf("args = %v, want [%s]", args, want)
+			}
+		})
+	}
+}
+
+// Ordinary tags must be unaffected.
+func TestBuildExifToolWriteArgs_AcceptsOrdinaryTags(t *testing.T) {
+	for _, key := range []string{"Author", "Title", "Subject", "Keywords", "Producer", "Creator"} {
+		t.Run(key, func(t *testing.T) {
+			_, err := buildExifToolWriteArgs(map[string]any{key: "value"})
+			if err != nil {
+				t.Fatalf("buildExifToolWriteArgs rejected the ordinary tag %q: %v", key, err)
+			}
+		})
+	}
+}

pkg/modules/libreoffice/api/api.go

@@ -353,7 +353,7 @@ func (a *Api) Descriptor() gotenberg.ModuleDescriptor {
 			fs.Duration("libreoffice-idle-shutdown-timeout", 0, "Shutdown LibreOffice after being idle for the given duration. Set to 0 to disable this feature")
 			fs.Bool("libreoffice-auto-start", false, "Automatically launch LibreOffice upon initialization if set to true; otherwise, LibreOffice will start at the time of the first conversion")
 			fs.Duration("libreoffice-start-timeout", time.Duration(20)*time.Second, "Maximum duration to wait for LibreOffice to start or restart")
-			fs.StringSlice("libreoffice-allow-list", []string{}, "Set the allowed URLs for LibreOffice outbound fetches (embedded images, linked content) using regular expressions - supports multiple values")
+			fs.StringSlice("libreoffice-allow-list", []string{}, `Set the allowed URLs for LibreOffice outbound fetches (embedded images, linked content) using regular expressions - supports multiple values. A match bypasses --libreoffice-deny-private-ips (LIBREOFFICE_DENY_PRIVATE_IPS) and --libreoffice-deny-public-ips (LIBREOFFICE_DENY_PUBLIC_IPS), so terminate the host or the pattern also matches suffix hosts, for example ^https?://internal\.svc(:|/|$)`)
 			fs.StringSlice("libreoffice-deny-list", []string{}, "Set the denied URLs for LibreOffice outbound fetches using regular expressions - supports multiple values")
 			fs.Bool("libreoffice-deny-private-ips", false, "Reject LibreOffice outbound URLs whose host resolves to a non-public IP address (loopback, RFC1918, link-local, unique-local). Enable on deployments that accept untrusted documents to mitigate SSRF against internal services")
 			fs.Bool("libreoffice-deny-public-ips", false, "Reject LibreOffice outbound URLs whose host resolves to a public IP address. Enable on air-gapped or data-governed deployments to prevent outbound traffic from leaving a private network")

pkg/modules/libreoffice/api/libreoffice.go

@@ -68,6 +68,59 @@ func (p *libreOfficeProcess) Start(logger *slog.Logger) error {
 
 	userProfileDirPath := p.fs.NewDirPath()
 
+	var (
+		cmd     *gotenberg.Cmd
+		success bool
+	)
+
+	// Registered here, right after the proxy starts listening, so that every
+	// failure below tears it down. A return between the proxy start and this
+	// point strands it: its listener stays bound, its Serve goroutine and HTTP
+	// client stay alive, and p.proxy is only assigned on success, so nothing
+	// could ever reach it to stop it. exec.Cmd.Start fails precisely under fd
+	// or memory pressure, and the supervisor retries the launch on the next
+	// request, so each stranded proxy compounds the condition that caused it.
+	defer func() {
+		if success {
+			p.cfgMu.Lock()
+			defer p.cfgMu.Unlock()
+
+			p.socketPort = port
+			p.userProfileDirPath = userProfileDirPath
+			p.cmd = cmd
+			p.proxy = proxy
+			p.isStarted.Store(true)
+
+			return
+		}
+
+		// LibreOffice failed to start; tear the proxy down too.
+		stopErr := proxy.Stop(context.Background())
+		if stopErr != nil {
+			logger.WarnContext(context.Background(), fmt.Sprintf("stop LibreOffice outbound proxy after failed start: %s", stopErr))
+		}
+
+		// Let's make sure the process is killed. It is nil when the failure
+		// happened before the command was built.
+		if cmd != nil {
+			killErr := cmd.Kill()
+			if killErr != nil {
+				logger.DebugContext(context.Background(), fmt.Sprintf("kill LibreOffice process: %v", killErr))
+			}
+		}
+
+		// And the user profile directory is deleted. It may never have been
+		// created, which RemoveAll reports as success.
+		removeErr := os.RemoveAll(userProfileDirPath)
+		if removeErr != nil {
+			logger.ErrorContext(context.Background(), fmt.Sprintf("remove LibreOffice's user profile directory: %v", removeErr))
+
+			return
+		}
+
+		logger.DebugContext(context.Background(), fmt.Sprintf("'%s' LibreOffice's user profile directory removed", userProfileDirPath))
+	}()
+
 	// LibreOffice fetches external content (OOXML images via
 	// TargetMode=External, RTF INCLUDEPICTURE, ODT linked images) inside
 	// its own libcurl. The profile config routes those fetches through the
@@ -75,7 +128,6 @@ func (p *libreOfficeProcess) Start(logger *slog.Logger) error {
 	// blocks content linked from untrusted locations so absolute-path
 	// (file://) and direct fetches are dropped at the source.
 	if err := writeSofficeProfileConfig(userProfileDirPath, proxy.Addr()); err != nil {
-		_ = proxy.Stop(context.Background())
 		return fmt.Errorf("write soffice profile config: %w", err)
 	}
 	sofficeEnv := sofficeProxyEnv(os.Environ(), proxy.Addr())
@@ -95,9 +147,8 @@ func (p *libreOfficeProcess) Start(logger *slog.Logger) error {
 	ctx, cancel := context.WithTimeout(context.Background(), p.arguments.startTimeout)
 	defer cancel()
 
-	cmd, err := gotenberg.CommandContext(ctx, logger, p.arguments.binPath, args...)
+	cmd, err = gotenberg.CommandContext(ctx, logger, p.arguments.binPath, args...)
 	if err != nil {
-		_ = proxy.Stop(context.Background())
 		return fmt.Errorf("create LibreOffice command: %w", err)
 	}
 	cmd.SetEnv(sofficeEnv)
@@ -106,7 +157,6 @@ func (p *libreOfficeProcess) Start(logger *slog.Logger) error {
 	// able to run as a daemon.
 	exitCode, err := cmd.Exec()
 	if err != nil && exitCode != 81 {
-		_ = proxy.Stop(context.Background())
 		return fmt.Errorf("execute LibreOffice: %w", err)
 	}
 
@@ -155,43 +205,6 @@ func (p *libreOfficeProcess) Start(logger *slog.Logger) error {
 		}
 	}()
 
-	var success bool
-
-	defer func() {
-		if success {
-			p.cfgMu.Lock()
-			defer p.cfgMu.Unlock()
-
-			p.socketPort = port
-			p.userProfileDirPath = userProfileDirPath
-			p.cmd = cmd
-			p.proxy = proxy
-			p.isStarted.Store(true)
-
-			return
-		}
-
-		// LibreOffice failed to start; tear the proxy down too.
-		stopErr := proxy.Stop(context.Background())
-		if stopErr != nil {
-			logger.WarnContext(context.Background(), fmt.Sprintf("stop LibreOffice outbound proxy after failed start: %s", stopErr))
-		}
-
-		// Let's make sure the process is killed.
-		err = cmd.Kill()
-		if err != nil {
-			logger.DebugContext(context.Background(), fmt.Sprintf("kill LibreOffice process: %v", err))
-		}
-
-		// And the user profile directory is deleted.
-		err = os.RemoveAll(userProfileDirPath)
-		if err != nil {
-			logger.ErrorContext(context.Background(), fmt.Sprintf("remove LibreOffice's user profile directory: %v", err))
-		}
-
-		logger.DebugContext(context.Background(), fmt.Sprintf("'%s' LibreOffice's user profile directory removed", userProfileDirPath))
-	}()
-
 	logger.DebugContext(context.Background(), "waiting for the LibreOffice socket to be available...")
 
 	for {

pkg/modules/libreoffice/api/protection.go

@@ -35,12 +35,13 @@ var (
 	zipMagic = []byte{0x50, 0x4b, 0x03, 0x04}
 
 	// An unencrypted OOXML document is always a ZIP package, so any of these
-	// extensions over a compound file means the payload is encrypted. Legacy
-	// binary formats (.doc, .xls, .ppt) are compound files either way and are
-	// deliberately absent.
+	// extensions over a compound file means the payload is encrypted. A .xlsb
+	// workbook stores binary parts inside that same ZIP package, so it belongs
+	// here too. Legacy binary formats (.doc, .xls, .ppt) are compound files
+	// either way and are deliberately absent.
 	ooxmlExtensions = map[string]struct{}{
 		".docx": {}, ".docm": {}, ".dotx": {}, ".dotm": {},
-		".xlsx": {}, ".xlsm": {}, ".xltx": {}, ".xltm": {},
+		".xlsx": {}, ".xlsm": {}, ".xltx": {}, ".xltm": {}, ".xlsb": {},
 		".pptx": {}, ".pptm": {}, ".potx": {}, ".potm": {},
 		".ppsx": {}, ".ppsm": {},
 	}

pkg/modules/libreoffice/api/protection_test.go

@@ -76,6 +76,11 @@ func TestDetectPasswordProtection(t *testing.T) {
 			path: ole2("encrypted.xlsx"),
 			want: PasswordProtectionRequired,
 		},
+		{
+			name: "encrypted binary workbook",
+			path: ole2("encrypted.xlsb"),
+			want: PasswordProtectionRequired,
+		},
 		{
 			name: "legacy binary document is inconclusive",
 			path: ole2("legacy.doc"),

pkg/modules/libreoffice/api/proxy.go

@@ -14,7 +14,7 @@ import (
 	"sync"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	"golang.org/x/net/http/httpproxy"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"

pkg/modules/libreoffice/api/proxy_test.go

@@ -17,14 +17,14 @@ import (
 	"testing"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 )
 
 func compileRegexes(t *testing.T, patterns ...string) []*regexp2.Regexp {
 	t.Helper()
 	out := make([]*regexp2.Regexp, 0, len(patterns))
 	for _, p := range patterns {
-		r, err := regexp2.Compile(p, 0)
+		r, err := regexp2.Compile(p, regexp2.None)
 		if err != nil {
 			t.Fatalf("compile %q: %v", p, err)
 		}
@@ -361,7 +361,7 @@ func TestSofficeProxyEnv_OverridesExisting(t *testing.T) {
 	// Old proxy values must be gone, not duplicated. Count exact-case keys.
 	counts := map[string]int{}
 	for _, kv := range out {
-		key := strings.SplitN(kv, "=", 2)[0]
+		key, _, _ := strings.Cut(kv, "=")
 		counts[key]++
 	}
 	for _, key := range []string{"http_proxy", "HTTP_PROXY", "https_proxy", "HTTPS_PROXY", "no_proxy", "NO_PROXY"} {

pkg/modules/libreoffice/routes.go

@@ -7,7 +7,7 @@ import (
 	"slices"
 	"strconv"
 
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
@@ -27,7 +27,7 @@ func convertRoute(libreOffice libreofficeapi.Uno, engine gotenberg.PdfEngine) ap
 		Method:      http.MethodPost,
 		Path:        "/forms/libreoffice/convert",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 			defaultOptions := libreofficeapi.DefaultOptions()
 

pkg/modules/libreoffice/routes_test.go

@@ -12,7 +12,7 @@ import (
 	"path/filepath"
 	"testing"
 
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"

pkg/modules/pdfcpu/optimize.go

@@ -180,7 +180,7 @@ func (engine *PdfCpu) listImages(ctx context.Context, inputPath string) ([]pdfcp
 // their second column is not a numeric object number.
 func parseImagesList(output string) []pdfcpuImage {
 	var images []pdfcpuImage
-	for _, line := range strings.Split(output, "\n") {
+	for line := range strings.SplitSeq(output, "\n") {
 		cols := strings.Split(line, "│")
 		if len(cols) < 9 {
 			continue

pkg/modules/pdfengines/concurrency.go

@@ -0,0 +1,172 @@
+package pdfengines
+
+import (
+	"sync"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
+)
+
+// defaultMaxConcurrency is the number of PDF files a single stub processes at
+// once when --pdfengines-max-concurrency (env PDFENGINES_MAX_CONCURRENCY) is
+// not set. Each unit of work forks an external binary (qpdf, pdfcpu, pdftk or
+// exiftool), so the ceiling trades wall clock against process count and RSS.
+//
+// It defaults to one, which processes files exactly as the sequential loops
+// this package used to run did. Raising it only ever affects a request that
+// carries several files, or one that splits into several outputs: a
+// single-file request never reaches the concurrent path at all. Operators who
+// send multi-file batches and have the memory headroom opt in.
+//
+// This never covers LibreOffice. libreoffice-pdfengine implements Convert and
+// nothing else, every other [gotenberg.PdfEngine] method on it returns
+// [gotenberg.ErrPdfEngineMethodNotSupported], and [ConvertStub] deliberately
+// does not use this package's helpers. A soffice instance costs too much
+// memory to run several of per container, so LibreOffice throughput is scaled
+// by adding Gotenberg containers, not by raising this number.
+const defaultMaxConcurrency = 1
+
+// maxFileConcurrency is how many files one request may have in flight at once.
+// It is replaced during [PdfEngines.Provision].
+var maxFileConcurrency = defaultMaxConcurrency
+
+// engineExtraSlots bounds the concurrency this package ADDS, across the whole
+// process rather than per request, and holds one fewer slot than
+// [maxFileConcurrency] because every request already owns one unit of its own.
+//
+// Bounding the added concurrency rather than the total is what keeps the
+// ceiling from becoming a throughput regression. The sequential loops this
+// helper replaced had no ceiling at all: X concurrent requests ran X engine
+// binaries, one apiece. A pool covering the total would cut those X requests
+// down to the ceiling, so an operator raising the flag to speed up a single
+// multi-file request would slow the server down under real load. Reserving
+// each request the unit it always had makes the worst case "what happened
+// before, plus at most maxFileConcurrency-1".
+//
+// A per-request limit would have the opposite failure: X simultaneous requests
+// forking X times the limit, trading the timeouts this exists to prevent for
+// memory exhaustion.
+var engineExtraSlots = make(chan struct{}, defaultMaxConcurrency-1)
+
+// acquireEngineSlot waits for the first unit of capacity to become available,
+// either this request's reserved unit or a slot from the shared pool, and
+// returns the function that gives it back.
+//
+// Waiting on both at once is the whole point. Committing to one source and
+// blocking on it strands the other: a goroutine parked on an exhausted pool
+// cannot pick up its own request's reserved unit when the file before it
+// finishes, so the reserved units sit idle while every file queues on the
+// pool, which is slower than having no pool at all.
+func acquireEngineSlot(ctx *api.Context, reserved chan struct{}) (func(), error) {
+	// An [api.Context] carries a request context in production, but one built
+	// as a literal, which the unit tests do, embeds a nil [context.Context]
+	// and would panic on Done. A nil channel never fires, which correctly
+	// leaves the two capacity sources as the only things to wait on.
+	var done <-chan struct{}
+	if ctx != nil && ctx.Context != nil {
+		done = ctx.Done()
+	}
+
+	// A select whose cancellation and capacity cases are both ready picks
+	// between them at random, so an already-dead request would start more
+	// files on a coin flip. Check first and stop taking on work.
+	if done != nil {
+		select {
+		case <-done:
+			return nil, ctx.Err()
+		default:
+		}
+	}
+
+	select {
+	case <-reserved:
+		return func() { reserved <- struct{}{} }, nil
+	case engineExtraSlots <- struct{}{}:
+		return func() { <-engineExtraSlots }, nil
+	case <-done:
+		return nil, ctx.Err()
+	}
+}
+
+// forEachInputPath runs fn against every input path, up to
+// --pdfengines-max-concurrency (env PDFENGINES_MAX_CONCURRENCY) at a time.
+//
+// The stubs mutate each PDF in place, so distinct input paths never touch the
+// same file and may run together. Callers that layer operations on one file,
+// like [WatermarkStub] applying several watermarks in order, must keep that
+// outer sequence and parallelize only the file dimension.
+//
+// Every path is attempted even after one fails, and the error returned is the
+// first in input order rather than the first to arrive. That keeps the failing
+// filename in the error message identical to what the sequential form
+// reported, which the integration scenarios assert on.
+func forEachInputPath(ctx *api.Context, inputPaths []string, fn func(inputPath string) error) error {
+	return forEachInputPathIndexed(ctx, inputPaths, func(_ int, inputPath string) error {
+		return fn(inputPath)
+	})
+}
+
+// forEachInputPathIndexed is [forEachInputPath] with the input path's index,
+// for callers collecting a result per file. Writing into a preallocated slice
+// at the given index needs no further synchronization; writing into a shared
+// map does and must not be done from fn.
+func forEachInputPathIndexed(ctx *api.Context, inputPaths []string, fn func(i int, inputPath string) error) error {
+	if len(inputPaths) == 0 {
+		return nil
+	}
+
+	// The common case is a single file. Skip the goroutine and the slot: the
+	// caller is already inside whatever bound its own route applies.
+	if len(inputPaths) == 1 {
+		return fn(0, inputPaths[0])
+	}
+
+	// At the default ceiling of one, run the plain sequential loop this helper
+	// replaced. Racing goroutines for a single slot would serialize the work
+	// just the same, but the order files are picked up in would be down to the
+	// scheduler, and every file would be attempted even once one has failed.
+	// Taking the old path keeps the default a genuine no-op: same order, same
+	// early return, no goroutines.
+	if maxFileConcurrency < 2 {
+		for i, inputPath := range inputPaths {
+			err := fn(i, inputPath)
+			if err != nil {
+				return err
+			}
+		}
+
+		return nil
+	}
+
+	// The unit this request would have had all to itself before any of this
+	// existed. Whichever file claims it runs without touching the shared pool,
+	// so concurrent requests can never throttle each other below the
+	// one-binary-apiece they already got. See [engineExtraSlots].
+	reserved := make(chan struct{}, 1)
+	reserved <- struct{}{}
+
+	errs := make([]error, len(inputPaths))
+
+	var wg sync.WaitGroup
+	for i, inputPath := range inputPaths {
+		wg.Go(func() {
+			release, err := acquireEngineSlot(ctx, reserved)
+			if err != nil {
+				errs[i] = err
+				return
+			}
+			defer release()
+
+			errs[i] = fn(i, inputPath)
+		})
+	}
+
+	wg.Wait()
+
+	for _, err := range errs {
+		if err != nil {
+			return err
+		}
+	}
+
+	return nil
+}

pkg/modules/pdfengines/concurrency_test.go

@@ -0,0 +1,341 @@
+package pdfengines
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"sync"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
+)
+
+func TestForEachInputPath(t *testing.T) {
+	for _, tc := range []struct {
+		scenario   string
+		inputPaths []string
+		fn         func(inputPath string) error
+		expectErr  string
+	}{
+		{
+			scenario:   "no input path",
+			inputPaths: nil,
+			fn:         func(string) error { return errors.New("must not run") },
+		},
+		{
+			scenario:   "single input path",
+			inputPaths: []string{"a.pdf"},
+			fn:         func(string) error { return nil },
+		},
+		{
+			scenario:   "single input path with error",
+			inputPaths: []string{"a.pdf"},
+			fn:         func(p string) error { return fmt.Errorf("boom %s", p) },
+			expectErr:  "boom a.pdf",
+		},
+		{
+			scenario:   "many input paths",
+			inputPaths: []string{"a.pdf", "b.pdf", "c.pdf", "d.pdf", "e.pdf"},
+			fn:         func(string) error { return nil },
+		},
+		{
+			scenario:   "error is the first in input order, not the first to arrive",
+			inputPaths: []string{"a.pdf", "b.pdf", "c.pdf"},
+			fn: func(p string) error {
+				// "c.pdf" fails without delay so that it lands well before
+				// "b.pdf"; the reported error must still be "b.pdf".
+				if p == "b.pdf" {
+					var counter int
+					for i := range 5_000_000 {
+						counter += i
+					}
+					return fmt.Errorf("slow failure %s (%d)", p, counter%1)
+				}
+				if p == "c.pdf" {
+					return fmt.Errorf("fast failure %s", p)
+				}
+				return nil
+			},
+			expectErr: "slow failure b.pdf (0)",
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			err := forEachInputPath(new(api.Context), tc.inputPaths, tc.fn)
+
+			if tc.expectErr == "" {
+				if err != nil {
+					t.Fatalf("expected no error but got: %v", err)
+				}
+				return
+			}
+
+			if err == nil {
+				t.Fatalf("expected error %q but got none", tc.expectErr)
+			}
+
+			if err.Error() != tc.expectErr {
+				t.Fatalf("expected error %q but got %q", tc.expectErr, err.Error())
+			}
+		})
+	}
+}
+
+func TestForEachInputPathRunsEveryPath(t *testing.T) {
+	inputPaths := make([]string, 50)
+	for i := range inputPaths {
+		inputPaths[i] = fmt.Sprintf("%d.pdf", i)
+	}
+
+	var (
+		mu   sync.Mutex
+		seen = make(map[string]int)
+	)
+
+	err := forEachInputPath(new(api.Context), inputPaths, func(inputPath string) error {
+		mu.Lock()
+		defer mu.Unlock()
+		seen[inputPath]++
+		return nil
+	})
+	if err != nil {
+		t.Fatalf("expected no error but got: %v", err)
+	}
+
+	if len(seen) != len(inputPaths) {
+		t.Fatalf("expected %d distinct paths but got %d", len(inputPaths), len(seen))
+	}
+
+	for path, count := range seen {
+		if count != 1 {
+			t.Fatalf("expected '%s' to run once but it ran %d times", path, count)
+		}
+	}
+}
+
+func TestForEachInputPathRespectsTheSlotCeiling(t *testing.T) {
+	previousSlots, previousMax := engineExtraSlots, maxFileConcurrency
+	defer func() { engineExtraSlots, maxFileConcurrency = previousSlots, previousMax }()
+
+	// One request may run its reserved unit plus ceiling-1 borrowed ones.
+	const ceiling = 3
+	maxFileConcurrency = ceiling
+	engineExtraSlots = make(chan struct{}, ceiling-1)
+
+	inputPaths := make([]string, 40)
+	for i := range inputPaths {
+		inputPaths[i] = fmt.Sprintf("%d.pdf", i)
+	}
+
+	var inFlight, peak atomic.Int64
+
+	err := forEachInputPath(new(api.Context), inputPaths, func(string) error {
+		current := inFlight.Add(1)
+		defer inFlight.Add(-1)
+
+		for {
+			observed := peak.Load()
+			if current <= observed || peak.CompareAndSwap(observed, current) {
+				break
+			}
+		}
+
+		// Hold the slot long enough that the ceiling would be exceeded if it
+		// were not enforced.
+		var counter int
+		for i := range 200_000 {
+			counter += i
+		}
+		_ = counter
+
+		return nil
+	})
+	if err != nil {
+		t.Fatalf("expected no error but got: %v", err)
+	}
+
+	if peak.Load() > ceiling {
+		t.Fatalf("expected at most %d concurrent runs but observed %d", ceiling, peak.Load())
+	}
+}
+
+func TestForEachInputPathHonorsCancellation(t *testing.T) {
+	previousSlots, previousMax := engineExtraSlots, maxFileConcurrency
+	defer func() { engineExtraSlots, maxFileConcurrency = previousSlots, previousMax }()
+
+	// Concurrent path, with the shared pool exhausted by another request, so
+	// only this request's reserved unit is available.
+	maxFileConcurrency = 3
+	engineExtraSlots = make(chan struct{}, 2)
+	engineExtraSlots <- struct{}{}
+	engineExtraSlots <- struct{}{}
+
+	cancelledCtx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	// Neither source of capacity is available: the pool is exhausted by other
+	// requests and this request's reserved unit is already in use by one of its
+	// own files. A waiter must observe the cancelled context rather than block
+	// forever. Driving acquireEngineSlot directly keeps that deterministic:
+	// through forEachInputPath the reserved unit is reusable, so whether a
+	// given file waits at all depends on how fast the file before it finishes.
+	inUse := make(chan struct{}, 1)
+
+	release, err := acquireEngineSlot(&api.Context{Context: cancelledCtx}, inUse)
+	if !errors.Is(err, context.Canceled) {
+		t.Fatalf("expected context.Canceled but got: %v", err)
+	}
+
+	if release != nil {
+		t.Fatal("expected no release function when acquisition fails")
+	}
+
+	// A cancelled request stops taking on work even when capacity is free,
+	// rather than deciding on the coin flip a ready select would give.
+	inUse <- struct{}{}
+
+	_, err = acquireEngineSlot(&api.Context{Context: cancelledCtx}, inUse)
+	if !errors.Is(err, context.Canceled) {
+		t.Fatalf("expected context.Canceled with the reserved unit free but got: %v", err)
+	}
+
+	// Live request, free reserved unit: acquired and handed back.
+	release, err = acquireEngineSlot(&api.Context{Context: context.Background()}, inUse)
+	if err != nil {
+		t.Fatalf("expected the reserved unit to be acquired but got: %v", err)
+	}
+
+	release()
+
+	if len(inUse) != 1 {
+		t.Fatalf("expected the reserved unit to be returned but the channel holds %d", len(inUse))
+	}
+}
+
+func TestForEachInputPathCompletesWithACancelledContext(t *testing.T) {
+	previousSlots, previousMax := engineExtraSlots, maxFileConcurrency
+	defer func() { engineExtraSlots, maxFileConcurrency = previousSlots, previousMax }()
+
+	maxFileConcurrency = 3
+	engineExtraSlots = make(chan struct{}, 2)
+	engineExtraSlots <- struct{}{}
+	engineExtraSlots <- struct{}{}
+
+	cancelledCtx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	done := make(chan struct{})
+
+	go func() {
+		defer close(done)
+		_ = forEachInputPath(&api.Context{Context: cancelledCtx}, []string{"a.pdf", "b.pdf", "c.pdf"}, func(string) error {
+			return nil
+		})
+	}()
+
+	select {
+	case <-done:
+	case <-time.After(10 * time.Second):
+		t.Fatal("forEachInputPath hung on a cancelled context with the shared pool exhausted")
+	}
+}
+
+func TestForEachInputPathNeverThrottlesBelowOnePerRequest(t *testing.T) {
+	previousSlots, previousMax := engineExtraSlots, maxFileConcurrency
+	defer func() { engineExtraSlots, maxFileConcurrency = previousSlots, previousMax }()
+
+	// A small ceiling against far more concurrent requests than it covers.
+	// Before the shared pool existed each of these ran a binary of its own, so
+	// the pool must not drop aggregate concurrency below one per request.
+	const (
+		ceiling  = 2
+		requests = 8
+	)
+
+	maxFileConcurrency = ceiling
+	engineExtraSlots = make(chan struct{}, ceiling-1)
+
+	// Every runner announces itself and then blocks, so the count of arrivals
+	// is the true simultaneous concurrency rather than whatever the scheduler
+	// happened to overlap.
+	arrived := make(chan struct{}, requests*3)
+	release := make(chan struct{})
+
+	var wg sync.WaitGroup
+	for range requests {
+		wg.Go(func() {
+			_ = forEachInputPath(new(api.Context), []string{"a.pdf", "b.pdf", "c.pdf"}, func(string) error {
+				arrived <- struct{}{}
+				<-release
+				return nil
+			})
+		})
+	}
+
+	// One runner per request must be able to start without waiting on the
+	// shared pool. If the pool governed the total instead of the surplus, only
+	// `ceiling` runners would ever arrive and this would time out.
+	for i := range requests {
+		select {
+		case <-arrived:
+		case <-time.After(10 * time.Second):
+			t.Fatalf("only %d runners started concurrently, expected at least one per request (%d); the shared pool is throttling requests against each other", i, requests)
+		}
+	}
+
+	close(release)
+	wg.Wait()
+}
+
+func TestForEachInputPathIsSequentialAtTheDefaultCeiling(t *testing.T) {
+	if defaultMaxConcurrency != 1 {
+		t.Fatalf("this test pins the default as a no-op, but defaultMaxConcurrency is %d", defaultMaxConcurrency)
+	}
+
+	previousSlots, previousMax := engineExtraSlots, maxFileConcurrency
+	defer func() { engineExtraSlots, maxFileConcurrency = previousSlots, previousMax }()
+
+	maxFileConcurrency = defaultMaxConcurrency
+	engineExtraSlots = make(chan struct{}, defaultMaxConcurrency-1)
+
+	// At the default the helper must behave exactly like the sequential loops
+	// it replaced: files in input order, and no file attempted once one has
+	// failed.
+	var order []string
+
+	err := forEachInputPath(new(api.Context), []string{"a.pdf", "b.pdf", "c.pdf", "d.pdf"}, func(inputPath string) error {
+		order = append(order, inputPath)
+		if inputPath == "b.pdf" {
+			return errors.New("boom")
+		}
+		return nil
+	})
+
+	if err == nil || err.Error() != "boom" {
+		t.Fatalf("expected error \"boom\" but got: %v", err)
+	}
+
+	if len(order) != 2 || order[0] != "a.pdf" || order[1] != "b.pdf" {
+		t.Fatalf("expected the run to stop after b.pdf in input order but got %v", order)
+	}
+}
+
+func TestForEachInputPathIndexed(t *testing.T) {
+	inputPaths := []string{"a.pdf", "b.pdf", "c.pdf", "d.pdf"}
+	collected := make([]string, len(inputPaths))
+
+	err := forEachInputPathIndexed(new(api.Context), inputPaths, func(i int, inputPath string) error {
+		collected[i] = inputPath
+		return nil
+	})
+	if err != nil {
+		t.Fatalf("expected no error but got: %v", err)
+	}
+
+	for i, inputPath := range inputPaths {
+		if collected[i] != inputPath {
+			t.Fatalf("expected index %d to hold '%s' but got '%s'", i, inputPath, collected[i])
+		}
+	}
+}

pkg/modules/pdfengines/pdfengines.go

@@ -45,6 +45,7 @@ type PdfEngines struct {
 	rotateNames         []string
 	facturXNames        []string
 	engines             []gotenberg.PdfEngine
+	maxConcurrency      int
 	disableRoutes       bool
 }
 
@@ -70,6 +71,7 @@ func (mod *PdfEngines) Descriptor() gotenberg.ModuleDescriptor {
 			fs.StringSlice("pdfengines-stamp-engines", []string{"pdfcpu", "pdftk"}, "Set the PDF engines and their order for the stamp feature - empty means all")
 			fs.StringSlice("pdfengines-rotate-engines", []string{"pdfcpu", "pdftk"}, "Set the PDF engines and their order for the rotate feature - empty means all")
 			fs.StringSlice("pdfengines-factur-x-engines", []string{"qpdf"}, "Set the PDF engines and their order for the Factur-X XMP feature - empty means all")
+			fs.Int("pdfengines-max-concurrency", defaultMaxConcurrency, "Set the maximum number of PDF files a feature processes concurrently, across all requests - bounds how many qpdf, pdfcpu, pdftk and exiftool processes run at once, so raising it trades memory for speed. Does not apply to LibreOffice: scale Gotenberg containers instead")
 			fs.Bool("pdfengines-disable-routes", false, "Disable the routes")
 
 			// Deprecated flags.
@@ -105,8 +107,16 @@ func (mod *PdfEngines) Provision(ctx *gotenberg.Context) error {
 	stampNames := flags.MustStringSlice("pdfengines-stamp-engines")
 	rotateNames := flags.MustStringSlice("pdfengines-rotate-engines")
 	facturXNames := flags.MustStringSlice("pdfengines-factur-x-engines")
+	mod.maxConcurrency = flags.MustInt("pdfengines-max-concurrency")
 	mod.disableRoutes = flags.MustBool("pdfengines-disable-routes")
 
+	if mod.maxConcurrency > 0 {
+		maxFileConcurrency = mod.maxConcurrency
+		// One fewer than the ceiling: each request already reserves a unit of
+		// its own. See [engineExtraSlots].
+		engineExtraSlots = make(chan struct{}, mod.maxConcurrency-1)
+	}
+
 	engines, err := ctx.Modules(new(gotenberg.PdfEngine))
 	if err != nil {
 		return fmt.Errorf("get PDF engines: %w", err)
@@ -222,6 +232,10 @@ func (mod *PdfEngines) Validate() error {
 		return errors.New("no PDF engine is available; enable at least one engine module (e.g. qpdf, pdfcpu, pdftk, libreoffice-pdfengine, exiftool)")
 	}
 
+	if mod.maxConcurrency < 1 {
+		return fmt.Errorf("PDF engines max concurrency must be at least 1, got %d; set --pdfengines-max-concurrency (env PDFENGINES_MAX_CONCURRENCY) to a positive value", mod.maxConcurrency)
+	}
+
 	availableEngines := make([]string, len(mod.engines))
 
 	for i, engine := range mod.engines {
@@ -296,6 +310,7 @@ func (mod *PdfEngines) SystemMessages() []string {
 		fmt.Sprintf("stamp engines - %s", strings.Join(mod.stampNames, " ")),
 		fmt.Sprintf("rotate engines - %s", strings.Join(mod.rotateNames, " ")),
 		fmt.Sprintf("factur-x engines - %s", strings.Join(mod.facturXNames, " ")),
+		fmt.Sprintf("max concurrency - %d", mod.maxConcurrency),
 	}
 }
 

pkg/modules/pdfengines/routes.go

@@ -11,7 +11,7 @@ import (
 	"strings"
 
 	"github.com/google/uuid"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
@@ -208,14 +208,14 @@ func RotateStub(ctx *api.Context, engine gotenberg.PdfEngine, angle int, pages s
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.Rotate(ctx, ctx.Log(), inputPath, angle, pages)
 		if err != nil {
 			return fmt.Errorf("rotate '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // ValidatePdfFormatsCompat checks for incompatible combinations of PDF formats
@@ -334,14 +334,14 @@ func SplitPdfStub(ctx *api.Context, engine gotenberg.PdfEngine, mode gotenberg.S
 // FlattenStub merges annotation appearances with page content for each given
 // PDF, effectively deleting the original annotations.
 func FlattenStub(ctx *api.Context, engine gotenberg.PdfEngine, inputPaths []string) error {
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.Flatten(ctx, ctx.Log(), inputPath)
 		if err != nil {
 			return fmt.Errorf("flatten '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // defaultImageQuality is the JPEG quality applied by the image optimization
@@ -393,19 +393,27 @@ func OptimizeStub(ctx *api.Context, engine gotenberg.PdfEngine, optimizeImages b
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.OptimizeImages(ctx, ctx.Log(), imageQuality, inputPath)
 		if err != nil {
 			return fmt.Errorf("optimize images of '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // ConvertStub transforms a given PDF to the specified formats defined in
 // [gotenberg.PdfFormats]. If no format, it does nothing and returns the input
 // paths.
+//
+// This loop stays sequential on purpose. Convert is the one PDF engine method
+// LibreOffice implements, and libreoffice-pdfengine is the default and only
+// convert engine, so every iteration here drives the single soffice daemon. A
+// LibreOffice instance is far too memory-hungry to run several of per
+// container: the way to convert more documents at once is to scale Gotenberg
+// containers, not to widen this loop. Do not route it through
+// [forEachInputPath].
 func ConvertStub(ctx *api.Context, engine gotenberg.PdfEngine, formats gotenberg.PdfFormats, inputPaths []string) ([]string, error) {
 	zeroValued := gotenberg.PdfFormats{}
 	if formats == zeroValued {
@@ -432,14 +440,14 @@ func WriteMetadataStub(ctx *api.Context, engine gotenberg.PdfEngine, metadata ma
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.WriteMetadata(ctx, ctx.Log(), metadata, inputPath)
 		if err != nil {
 			return fmt.Errorf("write metadata into '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // documentTitle returns the input PDF's Title metadata entry, falling back to
@@ -491,28 +499,33 @@ func WriteBookmarksStub(ctx *api.Context, engine gotenberg.PdfEngine, bookmarks
 			return nil
 		}
 
-		for _, inputPath := range inputPaths {
+		return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 			err := engine.WriteBookmarks(ctx, ctx.Log(), inputPath, b)
 			if err != nil {
 				return fmt.Errorf("write bookmarks into '%s': %w", inputPath, err)
 			}
-		}
+
+			return nil
+		})
 	case map[string][]gotenberg.Bookmark:
-		for _, inputPath := range inputPaths {
+		return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 			filename := ctx.OriginalFilename(inputPath)
-			if specificBookmarks, ok := b[filename]; ok {
-				err := engine.WriteBookmarks(ctx, ctx.Log(), inputPath, specificBookmarks)
-				if err != nil {
-					return fmt.Errorf("write bookmarks into '%s': %w", inputPath, err)
-				}
+			specificBookmarks, ok := b[filename]
+			if !ok {
+				return nil
 			}
-		}
+
+			err := engine.WriteBookmarks(ctx, ctx.Log(), inputPath, specificBookmarks)
+			if err != nil {
+				return fmt.Errorf("write bookmarks into '%s': %w", inputPath, err)
+			}
+
+			return nil
+		})
 	default:
 		// Should not happen.
 		return fmt.Errorf("bookmarks type '%T' not supported", bookmarks)
 	}
-
-	return nil
 }
 
 // FormDataPdfEmbeds extracts embedded file paths from form data.
@@ -537,14 +550,14 @@ func EmbedFilesMetadataStub(ctx *api.Context, engine gotenberg.PdfEngine, metada
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.EmbedFilesMetadata(ctx, ctx.Log(), metadata, inputPath)
 		if err != nil {
 			return fmt.Errorf("set embeds metadata on PDF '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // FormDataPdfFacturX extracts the Factur-X parameters and the invoice XML path
@@ -737,14 +750,14 @@ func InjectFacturXXMPStub(ctx *api.Context, engine gotenberg.PdfEngine, facturX
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.InjectFacturXXMP(ctx, ctx.Log(), facturX, inputPath)
 		if err != nil {
 			return fmt.Errorf("inject Factur-X XMP into PDF '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // FormDataPdfEncrypt extracts the encryption parameters and permissions from
@@ -783,14 +796,14 @@ func EncryptPdfStub(ctx *api.Context, engine gotenberg.PdfEngine, opts gotenberg
 		return nil
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.Encrypt(ctx, ctx.Log(), inputPath, opts)
 		if err != nil {
 			return fmt.Errorf("encrypt PDF '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // EmbedFilesStub embeds files into PDF files.
@@ -819,14 +832,14 @@ func EmbedFilesStub(ctx *api.Context, engine gotenberg.PdfEngine, embedPaths []s
 		resolvedPaths[i] = resolvedPath
 	}
 
-	for _, inputPath := range inputPaths {
+	return forEachInputPath(ctx, inputPaths, func(inputPath string) error {
 		err := engine.EmbedFiles(ctx, ctx.Log(), resolvedPaths, inputPath)
 		if err != nil {
 			return fmt.Errorf("embed files into PDF '%s': %w", inputPath, err)
 		}
-	}
 
-	return nil
+		return nil
+	})
 }
 
 // FormDataPdfStamps builds the ordered list of stamps from the repeated stamp
@@ -943,16 +956,23 @@ func bindStampOrWatermarkFiles(stamps []gotenberg.Stamp, files []string, kind st
 // WatermarkStub applies each watermark to a list of PDF files, in order.
 // Entries with no source are skipped, so an empty list does nothing.
 func WatermarkStub(ctx *api.Context, engine gotenberg.PdfEngine, watermarks []gotenberg.Stamp, inputPaths []string) error {
+	// Watermarks stack on the same file, so the outer loop stays sequential;
+	// only the file dimension is parallel.
 	for _, watermark := range watermarks {
 		if watermark.Source == "" {
 			continue
 		}
 
-		for _, inputPath := range inputPaths {
-			err := engine.Watermark(ctx, ctx.Log(), inputPath, watermark)
-			if err != nil {
-				return fmt.Errorf("watermark '%s': %w", inputPath, err)
+		err := forEachInputPath(ctx, inputPaths, func(inputPath string) error {
+			errWatermark := engine.Watermark(ctx, ctx.Log(), inputPath, watermark)
+			if errWatermark != nil {
+				return fmt.Errorf("watermark '%s': %w", inputPath, errWatermark)
 			}
+
+			return nil
+		})
+		if err != nil {
+			return err
 		}
 	}
 
@@ -962,16 +982,23 @@ func WatermarkStub(ctx *api.Context, engine gotenberg.PdfEngine, watermarks []go
 // StampStub applies each stamp to a list of PDF files, in order. Entries with
 // no source are skipped, so an empty list does nothing.
 func StampStub(ctx *api.Context, engine gotenberg.PdfEngine, stamps []gotenberg.Stamp, inputPaths []string) error {
+	// Stamps stack on the same file, so the outer loop stays sequential; only
+	// the file dimension is parallel.
 	for _, stamp := range stamps {
 		if stamp.Source == "" {
 			continue
 		}
 
-		for _, inputPath := range inputPaths {
-			err := engine.Stamp(ctx, ctx.Log(), inputPath, stamp)
-			if err != nil {
-				return fmt.Errorf("stamp '%s': %w", inputPath, err)
+		err := forEachInputPath(ctx, inputPaths, func(inputPath string) error {
+			errStamp := engine.Stamp(ctx, ctx.Log(), inputPath, stamp)
+			if errStamp != nil {
+				return fmt.Errorf("stamp '%s': %w", inputPath, errStamp)
 			}
+
+			return nil
+		})
+		if err != nil {
+			return err
 		}
 	}
 
@@ -984,7 +1011,7 @@ func mergeRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/merge",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1185,7 +1212,7 @@ func splitRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/split",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1337,7 +1364,7 @@ func flattenRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/flatten",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1372,7 +1399,7 @@ func optimizeRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/optimize",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1408,7 +1435,7 @@ func convertRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/convert",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1465,7 +1492,7 @@ func readMetadataRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/metadata/read",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			var inputPaths []string
@@ -1476,14 +1503,25 @@ func readMetadataRoute(engine gotenberg.PdfEngine) api.Route {
 				return fmt.Errorf("validate form data: %w", err)
 			}
 
-			res := make(map[string]map[string]any, len(inputPaths))
-			for _, inputPath := range inputPaths {
-				metadata, err := engine.ReadMetadata(ctx, ctx.Log(), inputPath)
-				if err != nil {
-					return fmt.Errorf("read metadata: %w", err)
+			// Collected per index, then folded into the map on this
+			// goroutine: a shared map cannot be written concurrently.
+			collected := make([]map[string]any, len(inputPaths))
+			err = forEachInputPathIndexed(ctx, inputPaths, func(i int, inputPath string) error {
+				metadata, errRead := engine.ReadMetadata(ctx, ctx.Log(), inputPath)
+				if errRead != nil {
+					return fmt.Errorf("read metadata: %w", errRead)
 				}
 
-				res[ctx.OriginalFilename(inputPath)] = metadata
+				collected[i] = metadata
+				return nil
+			})
+			if err != nil {
+				return err
+			}
+
+			res := make(map[string]map[string]any, len(inputPaths))
+			for i, inputPath := range inputPaths {
+				res[ctx.OriginalFilename(inputPath)] = collected[i]
 			}
 
 			err = c.JSON(http.StatusOK, res)
@@ -1508,7 +1546,7 @@ func writeMetadataRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/metadata/write",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1543,7 +1581,7 @@ func readBookmarksRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/bookmarks/read",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			var inputPaths []string
@@ -1554,14 +1592,25 @@ func readBookmarksRoute(engine gotenberg.PdfEngine) api.Route {
 				return fmt.Errorf("validate form data: %w", err)
 			}
 
-			res := make(map[string][]gotenberg.Bookmark, len(inputPaths))
-			for _, inputPath := range inputPaths {
-				bookmarks, err := engine.ReadBookmarks(ctx, ctx.Log(), inputPath)
-				if err != nil {
-					return fmt.Errorf("read bookmarks: %w", err)
+			// Collected per index, then folded into the map on this
+			// goroutine: a shared map cannot be written concurrently.
+			collected := make([][]gotenberg.Bookmark, len(inputPaths))
+			err = forEachInputPathIndexed(ctx, inputPaths, func(i int, inputPath string) error {
+				bookmarks, errRead := engine.ReadBookmarks(ctx, ctx.Log(), inputPath)
+				if errRead != nil {
+					return fmt.Errorf("read bookmarks: %w", errRead)
 				}
 
-				res[ctx.OriginalFilename(inputPath)] = bookmarks
+				collected[i] = bookmarks
+				return nil
+			})
+			if err != nil {
+				return err
+			}
+
+			res := make(map[string][]gotenberg.Bookmark, len(inputPaths))
+			for i, inputPath := range inputPaths {
+				res[ctx.OriginalFilename(inputPath)] = collected[i]
 			}
 
 			err = c.JSON(http.StatusOK, res)
@@ -1585,7 +1634,7 @@ func writeBookmarksRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/bookmarks/write",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1620,7 +1669,7 @@ func encryptRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/encrypt",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1665,7 +1714,7 @@ func embedRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/embed",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1727,7 +1776,7 @@ func watermarkRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/watermark",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1784,7 +1833,7 @@ func stampRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/stamp",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1843,7 +1892,7 @@ func rotateRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/rotate",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()
@@ -1880,7 +1929,7 @@ func facturXRoute(engine gotenberg.PdfEngine) api.Route {
 		Method:      http.MethodPost,
 		Path:        "/forms/pdfengines/factur-x",
 		IsMultipart: true,
-		Handler: func(c echo.Context) error {
+		Handler: func(c *echo.Context) error {
 			ctx := c.Get("context").(*api.Context)
 
 			form := ctx.FormData()

pkg/modules/prometheus/prometheus.go

@@ -7,7 +7,7 @@ import (
 	"net/http"
 	"time"
 
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 	"github.com/prometheus/client_golang/prometheus"
 	"github.com/prometheus/client_golang/prometheus/promhttp"
 	flag "github.com/spf13/pflag"

pkg/modules/qpdf/qpdf.go

@@ -120,6 +120,30 @@ func (engine *QPdf) spanAttrs(extra ...attribute.KeyValue) []attribute.KeyValue
 	return append(attrs, extra...)
 }
 
+// qpdfPageRange matches the page range syntax qpdf accepts, and nothing else.
+//
+// A term is a page number, "z" for the last page, or "rN" counting from the
+// end, optionally prefixed with "x" to exclude it. Terms combine into ranges
+// with "-", ranges join with ",", and the whole thing takes an optional ":odd"
+// or ":even".
+var qpdfPageRange = regexp.MustCompile(`^x?(?:z|r\d+|\d+)(?:-x?(?:z|r\d+|\d+))?(?:,x?(?:z|r\d+|\d+)(?:-x?(?:z|r\d+|\d+))?)*(?::odd|:even)?$`)
+
+// validateSplitSpan returns span when it is a qpdf page range.
+//
+// qpdf reads the argument after "--pages ." as either a page range or another
+// source file, so a span carrying a path makes qpdf append that file's pages
+// to the output. Other engines in the split chain accept spellings qpdf does
+// not, such as pdfcpu's "2-end", so a span this rejects is not necessarily
+// invalid. Returning an error lets the chain move on to an engine that
+// understands it.
+func validateSplitSpan(span string) error {
+	if qpdfPageRange.MatchString(span) {
+		return nil
+	}
+
+	return fmt.Errorf("split span '%s' is not a QPDF page range: %w", span, gotenberg.ErrPdfSplitModeNotSupported)
+}
+
 // Split splits a given PDF file.
 func (engine *QPdf) Split(ctx context.Context, logger *slog.Logger, mode gotenberg.SplitMode, inputPath, outputDirPath string) ([]string, error) {
 	ctx, span := gotenberg.Tracer().Start(ctx, "qpdf.Split",
@@ -139,6 +163,12 @@ func (engine *QPdf) Split(ctx context.Context, logger *slog.Logger, mode gotenbe
 			span.SetStatus(codes.Error, err.Error())
 			return nil, err
 		}
+		err := validateSplitSpan(mode.Span)
+		if err != nil {
+			span.RecordError(err)
+			span.SetStatus(codes.Error, err.Error())
+			return nil, err
+		}
 		args = append(args, inputPath)
 		args = append(args, engine.globalArgs...)
 		args = append(args, "--pages", ".", mode.Span)

pkg/modules/qpdf/qpdf_test.go

@@ -3,9 +3,12 @@ package qpdf
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"log/slog"
 	"os"
 	"testing"
+
+	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 )
 
 func TestStripQpdfStringPrefix(t *testing.T) {
@@ -270,3 +273,54 @@ func TestSetStreamSubtype(t *testing.T) {
 		}
 	})
 }
+
+func TestValidateSplitSpan(t *testing.T) {
+	for _, tc := range []struct {
+		span  string
+		valid bool
+	}{
+		// qpdf page ranges.
+		{"1", true},
+		{"12", true},
+		{"1-5", true},
+		{"2-z", true},
+		{"z", true},
+		{"r1", true},
+		{"r3-r1", true},
+		{"1,3,5-9", true},
+		{"1-5,x3", true},
+		{"1-z:odd", true},
+		{"1-z:even", true},
+
+		// Other engines' spellings. Not valid here, so the chain moves on.
+		{"2-end", false},
+		{"2-", false},
+		{"foo", false},
+
+		// A span qpdf would read as a source file.
+		{"/tmp/secret.pdf", false},
+		{"secret.pdf", false},
+		{"./secret.pdf", false},
+		{"../../etc/hosts", false},
+		{"1,/tmp/secret.pdf", false},
+		{"1 /tmp/secret.pdf", false},
+		{"", false},
+		{"--password=x", false},
+	} {
+		t.Run(tc.span, func(t *testing.T) {
+			err := validateSplitSpan(tc.span)
+			if tc.valid && err != nil {
+				t.Fatalf("validateSplitSpan(%q) = %v, want nil", tc.span, err)
+			}
+			if !tc.valid {
+				if err == nil {
+					t.Fatalf("validateSplitSpan(%q) = nil, want an error", tc.span)
+				}
+				// The chain must be able to try the next engine.
+				if !errors.Is(err, gotenberg.ErrPdfSplitModeNotSupported) {
+					t.Fatalf("error %v does not wrap ErrPdfSplitModeNotSupported", err)
+				}
+			}
+		})
+	}
+}

pkg/modules/webhook/client.go

@@ -11,7 +11,7 @@ import (
 	"time"
 
 	"github.com/hashicorp/go-retryablehttp"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 	"go.opentelemetry.io/otel"
 	"go.opentelemetry.io/otel/codes"
 	"go.opentelemetry.io/otel/propagation"
@@ -31,10 +31,33 @@ type client struct {
 	extraHttpHeaders map[string]string
 	startTime        time.Time
 
+	// deliveryTimeout bounds one delivery including retries. See
+	// [Webhook.deliveryTimeout].
+	deliveryTimeout time.Duration
+
 	client *retryablehttp.Client
 	logger *slog.Logger
 }
 
+// deliveryContext returns the context one delivery runs on.
+//
+// It keeps the values of ctx, so trace propagation and logging correlation
+// survive, and replaces its cancellation with a fresh budget. Threading the
+// conversion context straight through does not work: a delivery starts after
+// the handler returned, so that deadline may already be spent and the callback
+// would fail without a single attempt.
+func (c client) deliveryContext(ctx context.Context) (context.Context, context.CancelFunc) {
+	timeout := c.deliveryTimeout
+	if timeout <= 0 {
+		// An unset budget would expire the delivery before its first attempt.
+		// [Webhook.deliveryTimeout] never returns a non-positive value, so this
+		// only guards a caller that builds a client without one.
+		timeout = minDeliveryTimeout
+	}
+
+	return context.WithTimeout(context.WithoutCancel(ctx), timeout)
+}
+
 // send call the webhook either to send the success response or the error response.
 func (c client) send(ctx context.Context, body io.Reader, headers map[string]string, errored bool) error {
 	url := c.url
@@ -57,6 +80,9 @@ func (c client) send(ctx context.Context, body io.Reader, headers map[string]str
 		spanName = fmt.Sprintf("%s Webhook Error", method)
 	}
 
+	ctx, cancel := c.deliveryContext(ctx)
+	defer cancel()
+
 	tracer := gotenberg.Tracer()
 	ctx, span := tracer.Start(ctx, spanName,
 		trace.WithSpanKind(trace.SpanKindClient),
@@ -64,7 +90,10 @@ func (c client) send(ctx context.Context, body io.Reader, headers map[string]str
 	)
 	defer span.End()
 
-	req, err := retryablehttp.NewRequest(method, url, body)
+	// The request must carry ctx: retryablehttp.NewRequest builds on
+	// [context.Background], and its wait between attempts is a select on the
+	// request context, so a contextless request cannot be interrupted.
+	req, err := retryablehttp.NewRequestWithContext(ctx, method, url, body)
 	if err != nil {
 		span.RecordError(err)
 		span.SetStatus(codes.Error, err.Error())
@@ -114,13 +143,12 @@ func (c client) send(ctx context.Context, body io.Reader, headers map[string]str
 		return fmt.Errorf("send '%s' request to '%s': %w", method, url, err)
 	}
 
-	if resp.StatusCode >= http.StatusBadRequest {
-		err := fmt.Errorf("send '%s' request to '%s': got status: '%s'", method, url, resp.Status)
-		span.RecordError(err)
-		span.SetStatus(codes.Error, err.Error())
-		return err
-	}
-
+	// Registered before the status check below. [retryablehttp.Client.Do] hands
+	// back a live body for a status it does not retry, which is every 4xx but
+	// 429, so returning early without closing it strands the connection and the
+	// transport goroutines that serve it for the lifetime of the process. The
+	// transport is built per delivery in [gotenberg.NewOutboundHttpClient], so
+	// nothing reclaims it later either.
 	defer func() {
 		err := resp.Body.Close()
 		if err != nil {
@@ -128,6 +156,13 @@ func (c client) send(ctx context.Context, body io.Reader, headers map[string]str
 		}
 	}()
 
+	if resp.StatusCode >= http.StatusBadRequest {
+		err := fmt.Errorf("send '%s' request to '%s': got status: '%s'", method, url, resp.Status)
+		span.RecordError(err)
+		span.SetStatus(codes.Error, err.Error())
+		return err
+	}
+
 	// Last piece for calculating the latency.
 	finishTime := time.Now()
 
@@ -165,6 +200,9 @@ func (c client) sendEvent(ctx context.Context, correlationIdHeader, correlationI
 		return
 	}
 
+	ctx, cancel := c.deliveryContext(ctx)
+	defer cancel()
+
 	tracer := gotenberg.Tracer()
 	ctx, span := tracer.Start(ctx, "POST Webhook Event",
 		trace.WithSpanKind(trace.SpanKindClient),
@@ -172,7 +210,7 @@ func (c client) sendEvent(ctx context.Context, correlationIdHeader, correlationI
 	)
 	defer span.End()
 
-	req, err := retryablehttp.NewRequest(http.MethodPost, c.eventsUrl, b)
+	req, err := retryablehttp.NewRequestWithContext(ctx, http.MethodPost, c.eventsUrl, b)
 	if err != nil {
 		span.RecordError(err)
 		span.SetStatus(codes.Error, err.Error())

pkg/modules/webhook/middleware.go

@@ -14,7 +14,7 @@ import (
 	"time"
 
 	"github.com/hashicorp/go-retryablehttp"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
 	"github.com/gotenberg/gotenberg/v8/pkg/modules/api"
@@ -95,7 +95,7 @@ func webhookMiddleware(w *Webhook) api.Middleware {
 					})
 				}
 
-				return func(c echo.Context) error {
+				return func(c *echo.Context) error {
 					webhookUrl := c.Request().Header.Get("Gotenberg-Webhook-Url")
 					if webhookUrl == "" {
 						// No webhook URL, call the next middleware in the chain.
@@ -208,7 +208,7 @@ func webhookMiddleware(w *Webhook) api.Middleware {
 						}
 					}
 
-					// Retrieve values from echo.Context before it gets recycled.
+					// Retrieve values from [echo.Context] before it gets recycled.
 					// See https://github.com/gotenberg/gotenberg/issues/1000.
 					startTime := c.Get("startTime").(time.Time)
 					correlationIdHeader := c.Get("correlationIdHeader").(string)
@@ -222,6 +222,7 @@ func webhookMiddleware(w *Webhook) api.Middleware {
 						eventsUrl:        webhookEventsUrl,
 						extraHttpHeaders: extraHttpHeaders,
 						startTime:        startTime,
+						deliveryTimeout:  w.deliveryTimeout(),
 
 						client: &retryablehttp.Client{
 							HTTPClient:   gotenberg.NewOutboundHttpClient(w.clientTimeout, w.allowList, w.denyList, w.enableEnvironmentProxy, ipOpts...),
@@ -230,7 +231,10 @@ func webhookMiddleware(w *Webhook) api.Middleware {
 							RetryWaitMax: w.retryMaxWait,
 							Logger:       gotenberg.NewLeveledLogger(ctx.Log()),
 							CheckRetry:   retryablehttp.DefaultRetryPolicy,
-							Backoff:      retryablehttp.DefaultBackoff,
+							// Not DefaultBackoff: it returns a remote Retry-After
+							// verbatim, ignoring --webhook-retry-max-wait (env
+							// WEBHOOK_RETRY_MAX_WAIT).
+							Backoff: gotenberg.ClampedBackoff,
 						},
 						logger: ctx.Log(),
 					}
@@ -319,16 +323,16 @@ func webhookMiddleware(w *Webhook) api.Middleware {
 					// As a webhook URL has been given, we handle the request in a
 					// goroutine and return immediately.
 					//
-					// Echo returns the echo.Context back to its sync.Pool as
+					// Echo returns the [echo.Context] back to its sync.Pool as
 					// soon as this synchronous handler returns ErrAsyncProcess.
 					// A concurrent request can then claim the recycled context
 					// and c.Reset() wipes the shared store, which would cause
 					// any c.Get("...").(T) assertion downstream of the webhook
 					// goroutine to panic on a nil value and crash the process.
 					// Snapshot the keys downstream reads onto a detached
-					// wrapper before spawning the goroutine so pool reuse
+					// context before spawning the goroutine so pool reuse
 					// cannot reach into our async work.
-					detached := newPoolSafeContext(c, "logger", "context", "correlationId", "correlationIdHeader", "startTime")
+					detached := newDetachedContext(c, "logger", "context", "correlationId", "correlationIdHeader", "startTime")
 
 					w.asyncCount.Add(1)
 					go func() {

pkg/modules/webhook/pool_safe_context.go

@@ -1,58 +1,34 @@
 package webhook
 
 import (
-	"sync"
-
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 )
 
-// poolSafeContext wraps an [echo.Context] and keeps a private snapshot of
-// the values that downstream middleware and route handlers read from the
-// store. Echo returns an [echo.Context] to its sync.Pool as soon as the
-// synchronous handler returns, including when the webhook middleware
-// returns [api.ErrAsyncProcess]. A concurrent request can then claim the
-// recycled context and c.Reset() wipes the shared store out from under
-// the webhook goroutine, which causes any
-// `c.Get("logger").(*slog.Logger)`-style assertion further down the
-// chain to panic on a nil value.
+// newDetachedContext returns an [echo.Context] carrying a snapshot of the given
+// keys, detached from Echo's context pool.
 //
-// Wrapping c before handing it to the goroutine insulates the async work
-// from pool reuse: Get/Set read and write the private store while every
-// other [echo.Context] method delegates to the embedded context for
-// anything the downstream might still need.
-type poolSafeContext struct {
-	echo.Context
-	mu    sync.RWMutex
-	store map[string]any
-}
-
-// newPoolSafeContext snapshots the given keys from c into a detached
-// store and returns a wrapper whose Get/Set operate on that store
-// exclusively. Keys absent from c are omitted; the wrapper still
+// Echo returns an [echo.Context] to its sync.Pool as soon as the synchronous
+// handler returns, including when the webhook middleware returns
+// [api.ErrAsyncProcess]. A concurrent request can then claim the recycled
+// context and c.Reset() wipes the shared store out from under the webhook
+// goroutine, which causes any `c.Get("logger").(*slog.Logger)`-style assertion
+// further down the chain to panic on a nil value.
+//
+// [echo.NewContext] allocates outside the pool, so recycling cannot reach the
+// returned context. Keys absent from c are omitted; the returned context still
 // returns nil for them, matching [echo.Context.Get] behavior.
-func newPoolSafeContext(c echo.Context, keys ...string) *poolSafeContext {
-	store := make(map[string]any, len(keys))
+//
+// Only the asynchronous path uses this. Nothing downstream of the webhook
+// middleware writes to the response: contextMiddleware sits upstream and has
+// already answered 204 by the time the goroutine runs.
+func newDetachedContext(c *echo.Context, keys ...string) *echo.Context {
+	detached := echo.NewContext(c.Request(), c.Response(), c.Echo())
+
 	for _, key := range keys {
 		if v := c.Get(key); v != nil {
-			store[key] = v
+			detached.Set(key, v)
 		}
 	}
-	return &poolSafeContext{Context: c, store: store}
-}
 
-// Get returns the value stored in the detached store, not the embedded
-// context's pooled store.
-func (p *poolSafeContext) Get(key string) any {
-	p.mu.RLock()
-	defer p.mu.RUnlock()
-	return p.store[key]
-}
-
-// Set writes to the detached store, not the embedded context's pooled
-// store. This prevents downstream middleware writes from leaking into a
-// later request that claims the same pooled context.
-func (p *poolSafeContext) Set(key string, val any) {
-	p.mu.Lock()
-	defer p.mu.Unlock()
-	p.store[key] = val
+	return detached
 }

pkg/modules/webhook/pool_safe_context_test.go

@@ -6,10 +6,10 @@ import (
 	"net/http/httptest"
 	"testing"
 
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 )
 
-func TestPoolSafeContext_SurvivesUnderlyingReset(t *testing.T) {
+func TestNewDetachedContext_SurvivesUnderlyingReset(t *testing.T) {
 	e := echo.New()
 	req := httptest.NewRequest(http.MethodPost, "/", nil)
 	rec := httptest.NewRecorder()
@@ -19,10 +19,10 @@ func TestPoolSafeContext_SurvivesUnderlyingReset(t *testing.T) {
 	c.Set("logger", logger)
 	c.Set("correlationId", "abc-123")
 
-	detached := newPoolSafeContext(c, "logger", "correlationId", "missing")
+	detached := newDetachedContext(c, "logger", "correlationId", "missing")
 
-	// Simulate Echo recycling c for a concurrent request. Reset wipes the
-	// shared store, which is exactly the crash scenario the wrapper
+	// Simulate Echo recycling c for a concurrent request. Reset clears the
+	// pooled store, which is exactly the crash scenario the detached context
 	// guards against.
 	c.Reset(httptest.NewRequest(http.MethodGet, "/", nil), httptest.NewRecorder())
 
@@ -38,17 +38,17 @@ func TestPoolSafeContext_SurvivesUnderlyingReset(t *testing.T) {
 
 	// Underlying c must remain clean.
 	if c.Get("logger") != nil {
-		t.Fatalf("underlying c.Get(\"logger\") leaked wrapper state after reset")
+		t.Fatalf("underlying c.Get(\"logger\") leaked detached state after reset")
 	}
 }
 
-func TestPoolSafeContext_SetDoesNotTouchUnderlying(t *testing.T) {
+func TestNewDetachedContext_SetDoesNotTouchUnderlying(t *testing.T) {
 	e := echo.New()
 	req := httptest.NewRequest(http.MethodPost, "/", nil)
 	rec := httptest.NewRecorder()
 	c := e.NewContext(req, rec)
 
-	detached := newPoolSafeContext(c)
+	detached := newDetachedContext(c)
 	detached.Set("foo", "bar")
 
 	if got, _ := detached.Get("foo").(string); got != "bar" {

pkg/modules/webhook/webhook.go

@@ -5,7 +5,7 @@ import (
 	"sync/atomic"
 	"time"
 
-	"github.com/dlclark/regexp2"
+	"github.com/dlclark/regexp2/v2"
 	flag "github.com/spf13/pflag"
 
 	"github.com/gotenberg/gotenberg/v8/pkg/gotenberg"
@@ -42,7 +42,7 @@ func (w *Webhook) Descriptor() gotenberg.ModuleDescriptor {
 		FlagSet: func() *flag.FlagSet {
 			fs := flag.NewFlagSet("webhook", flag.ExitOnError)
 			fs.Bool("webhook-enable-sync-mode", false, "Enable synchronous mode for the webhook feature")
-			fs.StringSlice("webhook-allow-list", []string{}, "Set the allowed URLs for the webhook feature using regular expressions - supports multiple values")
+			fs.StringSlice("webhook-allow-list", []string{}, `Set the allowed URLs for the webhook feature using regular expressions - supports multiple values. A match bypasses --webhook-deny-private-ips (WEBHOOK_DENY_PRIVATE_IPS) and --webhook-deny-public-ips (WEBHOOK_DENY_PUBLIC_IPS), so terminate the host or the pattern also matches suffix hosts, for example ^https?://internal\.svc(:|/|$)`)
 			fs.StringSlice("webhook-deny-list", []string{}, "Set the denied URLs for the webhook feature using regular expressions - supports multiple values")
 			fs.Bool("webhook-deny-private-ips", false, "Reject webhook URLs whose host resolves to a non-public IP address (loopback, RFC1918, link-local, unique-local). Enable on deployments that accept untrusted webhook destinations to mitigate SSRF against internal services")
 			fs.Bool("webhook-deny-public-ips", false, "Reject webhook URLs whose host resolves to a public IP address. Enable on air-gapped or data-governed deployments to prevent callbacks from leaving a private network")
@@ -50,7 +50,7 @@ func (w *Webhook) Descriptor() gotenberg.ModuleDescriptor {
 			fs.Int("webhook-max-retry", 4, "Set the maximum number of retries for the webhook feature")
 
 			// Deprecated flags.
-			fs.StringSlice("webhook-error-allow-list", []string{}, "Set the allowed URLs in case of an error for the webhook feature using regular expressions - supports multiple values")
+			fs.StringSlice("webhook-error-allow-list", []string{}, `Set the allowed URLs in case of an error for the webhook feature using regular expressions - supports multiple values. A match bypasses --webhook-deny-private-ips (WEBHOOK_DENY_PRIVATE_IPS) and --webhook-deny-public-ips (WEBHOOK_DENY_PUBLIC_IPS), so terminate the host or the pattern also matches suffix hosts, for example ^https?://internal\.svc(:|/|$)`)
 			fs.StringSlice("webhook-error-deny-list", []string{}, "Set the denied URLs in case of an error for the webhook feature using regular expressions - supports multiple values")
 			err := fs.MarkDeprecated("webhook-error-allow-list", "use --webhook-allow-list instead")
 			if err != nil {
@@ -92,6 +92,27 @@ func (w *Webhook) Provision(ctx *gotenberg.Context) error {
 	return nil
 }
 
+// minDeliveryTimeout is the floor for [Webhook.deliveryTimeout], so that a
+// deliberately tiny --webhook-client-timeout (env WEBHOOK_CLIENT_TIMEOUT) never
+// leaves a delivery with no budget at all.
+const minDeliveryTimeout = 1 * time.Second
+
+// deliveryTimeout bounds one webhook delivery including its retries. It is the
+// worst case a correctly behaving remote produces: one client timeout per
+// attempt, plus the capped wait between attempts.
+//
+// A delivery runs after the handler returned, so it cannot borrow the
+// conversion deadline. Without this budget it would have none, because
+// [retryablehttp] builds its requests on [context.Background].
+func (w *Webhook) deliveryTimeout() time.Duration {
+	timeout := w.clientTimeout*time.Duration(w.maxRetry+1) + w.retryMaxWait*time.Duration(w.maxRetry)
+	if timeout < minDeliveryTimeout {
+		return minDeliveryTimeout
+	}
+
+	return timeout
+}
+
 // Middlewares returns the middleware.
 func (w *Webhook) Middlewares() ([]api.Middleware, error) {
 	if w.disable {

pkg/modules/webhook/webhook_test.go

@@ -0,0 +1,95 @@
+package webhook
+
+import (
+	"context"
+	"testing"
+	"time"
+)
+
+func TestWebhook_deliveryTimeout(t *testing.T) {
+	for _, tc := range []struct {
+		scenario      string
+		clientTimeout time.Duration
+		maxRetry      int
+		retryMaxWait  time.Duration
+		want          time.Duration
+	}{
+		{
+			scenario:      "shipped defaults",
+			clientTimeout: 30 * time.Second,
+			maxRetry:      4,
+			retryMaxWait:  30 * time.Second,
+			want:          270 * time.Second,
+		},
+		{
+			scenario:      "no retry is one client timeout",
+			clientTimeout: 30 * time.Second,
+			maxRetry:      0,
+			retryMaxWait:  30 * time.Second,
+			want:          30 * time.Second,
+		},
+		{
+			scenario:      "a zero client timeout still gets a budget",
+			clientTimeout: 0,
+			maxRetry:      0,
+			retryMaxWait:  0,
+			want:          minDeliveryTimeout,
+		},
+	} {
+		t.Run(tc.scenario, func(t *testing.T) {
+			w := &Webhook{
+				clientTimeout: tc.clientTimeout,
+				maxRetry:      tc.maxRetry,
+				retryMaxWait:  tc.retryMaxWait,
+			}
+			if got := w.deliveryTimeout(); got != tc.want {
+				t.Fatalf("deliveryTimeout() = %s, want %s", got, tc.want)
+			}
+			if w.deliveryTimeout() <= 0 {
+				t.Fatal("deliveryTimeout() must always be positive")
+			}
+		})
+	}
+}
+
+// A delivery must not inherit the conversion deadline. It runs after the
+// handler returned, so that deadline is often already spent, which would fail
+// the callback without a single attempt.
+func TestClient_deliveryContext_IgnoresAnExpiredParentDeadline(t *testing.T) {
+	expired, cancelExpired := context.WithTimeout(context.Background(), -1*time.Second)
+	defer cancelExpired()
+
+	if expired.Err() == nil {
+		t.Fatal("expected the parent context to be expired")
+	}
+
+	c := client{deliveryTimeout: 30 * time.Second}
+	ctx, cancel := c.deliveryContext(expired)
+	defer cancel()
+
+	if ctx.Err() != nil {
+		t.Fatalf("delivery context inherited the expired parent: %v", ctx.Err())
+	}
+
+	deadline, ok := ctx.Deadline()
+	if !ok {
+		t.Fatal("delivery context has no deadline, so a delivery would be unbounded")
+	}
+	if remaining := time.Until(deadline); remaining <= 0 {
+		t.Fatalf("delivery budget = %s, want a positive value", remaining)
+	}
+}
+
+// The delivery context must still be bounded, so a hostile remote cannot hold
+// the goroutine and its output file open indefinitely.
+func TestClient_deliveryContext_IsBounded(t *testing.T) {
+	c := client{deliveryTimeout: 50 * time.Millisecond}
+	ctx, cancel := c.deliveryContext(context.Background())
+	defer cancel()
+
+	select {
+	case <-ctx.Done():
+	case <-time.After(5 * time.Second):
+		t.Fatal("delivery context never expired")
+	}
+}

test/integration/features/chromium_convert_url.feature

@@ -589,7 +589,7 @@ Feature: /forms/chromium/convert/url
   @chromium-ssrf
   Scenario: POST /forms/chromium/convert/url (Redirect to a non-allow-listed address is re-filtered)
     Given I have a Gotenberg container with the following environment variable(s):
-      | CHROMIUM_ALLOW_LIST | ^https?://host.docker.internal.* |
+      | CHROMIUM_ALLOW_LIST | ^https?://host\\.docker\\.internal(:[0-9]+)?/ |
     Given I have a static server
     When I make a "POST" request to Gotenberg at the "/forms/chromium/convert/url" endpoint with the following form data and header(s):
       | url | http://host.docker.internal:%d/redirect-to-private | field |
@@ -1401,3 +1401,19 @@ Feature: /forms/chromium/convert/url
     Then the response header "Content-Type" should be "application/pdf"
     Then there should be 1 PDF(s) in the response
     Then the "foo.pdf" PDF should have 1 page(s)
+
+  # chrome://crash makes the renderer crash deterministically, the same
+  # failure class as a renderer crash triggered by the page content. The
+  # request must fail fast with a 503 instead of hanging until the API
+  # timeout.
+  # See https://github.com/gotenberg/gotenberg/issues/1640.
+  Scenario: POST /forms/chromium/convert/url (Chromium crash fails fast with 503)
+    Given I have a default Gotenberg container
+    When I make a "POST" request to Gotenberg at the "/forms/chromium/convert/url" endpoint with the following form data and header(s):
+      | url | chrome://crash | field |
+    Then the response status code should be 503
+    Then the response header "Content-Type" should be "text/plain; charset=UTF-8"
+    Then the response body should contain string:
+      """
+      Chromium crashed while processing the request
+      """

test/integration/features/health.feature

@@ -1,6 +1,5 @@
 # TODO:
 # 1. Check if down for each module.
-# 2. Restarting modules do not make health check fail.
 
 @health
 Feature: /health
@@ -106,7 +105,19 @@ Feature: /health
     When I make a "HEAD" request to Gotenberg at the "/foo/health" endpoint
     Then the response status code should be 200
 
+  # A planned restart, the eager cycle after LIBREOFFICE_RESTART_AFTER
+  # conversions, must not fail the health check: requests arriving during it
+  # are requeued, not rejected. Setting the limit to 1 restarts LibreOffice
+  # after every conversion, so each probe lands right on a restart.
+  # See https://github.com/gotenberg/gotenberg/issues/1648.
+  Scenario: GET /health (Planned LibreOffice Restart)
+    Given I have a Gotenberg container with the following environment variable(s):
+      | LIBREOFFICE_RESTART_AFTER | 1 |
+    When I make 5 sequential "POST" requests to Gotenberg at the "/forms/libreoffice/convert" endpoint, probing "/health" after each, with the following form data and header(s):
+      | files | testdata/page_1.docx | file |
+    Then all sequential response status codes should be 200
+    Then all probe response status codes should be 200
+
 
 # TODO:
-# 1. Check if down for each module.
-# 2. Restarting modules do not make health check fail.
+# 1. Check if down for each module.

test/integration/scenario/containers.go

@@ -11,7 +11,6 @@ import (
 	"github.com/moby/moby/client"
 	"github.com/testcontainers/testcontainers-go"
 	"github.com/testcontainers/testcontainers-go/exec"
-	"github.com/testcontainers/testcontainers-go/network"
 	"github.com/testcontainers/testcontainers-go/wait"
 )
 
@@ -21,11 +20,13 @@ import (
 const testcontainersLabel = "org.testcontainers"
 
 // PruneOrphanedNetworks removes dangling networks created by the test suite.
-// Each scenario spins a dedicated network, and a failed container start can
-// leak one before teardown records it. Leaked networks consume Docker's
-// predefined address pools until none remain and every later scenario fails
-// with "all predefined address pools have been fully subnetted". Call this
-// before a run and between retries to reclaim the subnets.
+// Scenarios no longer create one: the Gotenberg container is reached over its
+// mapped port and the host-side helper over host.docker.internal, so the
+// default bridge suffices. This stays as cheap insurance against networks
+// leaked by an older suite version or an interrupted run, which consume
+// Docker's predefined address pools until none remain and every later
+// scenario fails with "all predefined address pools have been fully
+// subnetted".
 //
 // Only unused networks bearing the testcontainers label are removed, so
 // running containers and operator networks are never affected.
@@ -99,17 +100,18 @@ func applyDefaultEnv(env map[string]string) map[string]string {
 	return env
 }
 
-func startGotenbergContainer(ctx context.Context, env map[string]string) (*testcontainers.DockerNetwork, testcontainers.Container, error) {
+// startGotenbergContainer starts a Gotenberg container on Docker's default
+// bridge. No dedicated network is created: the suite addresses the container
+// through container.Host plus its mapped port, and the container reaches the
+// host-side webhook and static file server through the host.docker.internal
+// alias below, so a per-scenario network would carry no traffic while still
+// consuming one of Docker's predefined subnets.
+func startGotenbergContainer(ctx context.Context, env map[string]string) (testcontainers.Container, error) {
 	ctx, cancel := context.WithTimeout(ctx, 2*time.Minute)
 	defer cancel()
 
 	env = applyDefaultEnv(env)
 
-	n, err := network.New(ctx)
-	if err != nil {
-		return nil, nil, fmt.Errorf("create Gotenberg container network: %w", err)
-	}
-
 	healthPath := "/health"
 	if env["API_ROOT_PATH"] != "" {
 		healthPath = fmt.Sprintf("%shealth", env["API_ROOT_PATH"])
@@ -122,7 +124,6 @@ func startGotenbergContainer(ctx context.Context, env map[string]string) (*testc
 		HostConfigModifier: func(hostConfig *container.HostConfig) {
 			hostConfig.ExtraHosts = []string{"host.docker.internal:host-gateway"}
 		},
-		Networks:   []string{n.Name},
 		WaitingFor: wait.ForHTTP(healthPath),
 		Env:        env,
 	}
@@ -148,19 +149,10 @@ func startGotenbergContainer(ctx context.Context, env map[string]string) (*testc
 			}
 		}
 
-		// The network is already created. The scenario teardown only
-		// removes networks it knows about, and the caller discards n on
-		// error, so remove it here to avoid leaking a subnet on every
-		// failed start. Leaked networks accumulate until Docker's address
-		// pools are fully subnetted and all later scenarios fail.
-		if errRemove := n.Remove(ctx); errRemove != nil {
-			err = fmt.Errorf("%w (also failed to remove network: %v)", err, errRemove)
-		}
-
-		return nil, nil, err
+		return nil, err
 	}
 
-	return n, c, nil
+	return c, nil
 }
 
 func execCommandInIntegrationToolsContainer(ctx context.Context, cmd []string, path string) (string, error) {

test/integration/scenario/scenario.go

@@ -86,19 +86,22 @@ func findScenarioLine(filePath, name string) int {
 }
 
 type scenario struct {
-	resp                      *httptest.ResponseRecorder
-	concurrentResps           []*httptest.ResponseRecorder
-	workdir                   string
-	teststoreDir              string
-	gotenbergContainer        testcontainers.Container
-	gotenbergContainerNetwork *testcontainers.DockerNetwork
-	server                    *server
-	hostPort                  int
+	resp               *httptest.ResponseRecorder
+	concurrentResps    []*httptest.ResponseRecorder
+	probeResps         []*httptest.ResponseRecorder
+	sequentialResps    []*httptest.ResponseRecorder
+	workdir            string
+	teststoreDir       string
+	gotenbergContainer testcontainers.Container
+	server             *server
+	hostPort           int
 }
 
 func (s *scenario) reset(ctx context.Context) error {
 	s.resp = httptest.NewRecorder()
 	s.concurrentResps = nil
+	s.probeResps = nil
+	s.sequentialResps = nil
 
 	err := os.RemoveAll(s.workdir)
 	if err != nil {
@@ -119,11 +122,10 @@ func (s *scenario) reset(ctx context.Context) error {
 }
 
 func (s *scenario) iHaveADefaultGotenbergContainer(ctx context.Context) error {
-	n, c, err := startGotenbergContainer(ctx, nil)
+	c, err := startGotenbergContainer(ctx, nil)
 	if err != nil {
 		return fmt.Errorf("create Gotenberg container: %s", err)
 	}
-	s.gotenbergContainerNetwork = n
 	s.gotenbergContainer = c
 	return nil
 }
@@ -133,11 +135,10 @@ func (s *scenario) iHaveAGotenbergContainerWithTheFollowingEnvironmentVariables(
 	for _, row := range envTable.Rows {
 		env[row.Cells[0].Value] = row.Cells[1].Value
 	}
-	n, c, err := startGotenbergContainer(ctx, env)
+	c, err := startGotenbergContainer(ctx, env)
 	if err != nil {
 		return fmt.Errorf("create Gotenberg container: %s", err)
 	}
-	s.gotenbergContainerNetwork = n
 	s.gotenbergContainer = c
 	return nil
 }
@@ -470,6 +471,130 @@ func (s *scenario) iMakeConcurrentRequestsToGotenberg(ctx context.Context, count
 	return nil
 }
 
+// iMakeSequentialRequestsToGotenbergProbing mirrors the client loop from
+// https://github.com/gotenberg/gotenberg/issues/1648: a conversion, then a
+// probe, repeated. It records both the conversion and the probe responses so a
+// scenario can assert that a planned process restart neither fails the probe
+// nor breaks the conversions. Requests are sequential on purpose, since the bug
+// only surfaces between two conversions.
+func (s *scenario) iMakeSequentialRequestsToGotenbergProbing(ctx context.Context, count int, method, endpoint, probeEndpoint string, dataTable *godog.Table) error {
+	if s.gotenbergContainer == nil {
+		return errors.New("no Gotenberg container")
+	}
+
+	fields := make(map[string][]string)
+	files := make(map[string][]string)
+	headers := make(map[string]string)
+
+	for _, row := range dataTable.Rows {
+		name := row.Cells[0].Value
+		value := row.Cells[1].Value
+		kind := row.Cells[2].Value
+
+		switch kind {
+		case "field":
+			fields[name] = append(fields[name], value)
+		case "file":
+			wd, err := os.Getwd()
+			if err != nil {
+				return fmt.Errorf("get current directory: %w", err)
+			}
+			value = fmt.Sprintf("%s/%s", wd, value)
+			files[name] = append(files[name], value)
+		case "header":
+			headers[name] = value
+		default:
+			return fmt.Errorf("unexpected %q %q", kind, value)
+		}
+	}
+
+	base, err := containerHttpEndpoint(ctx, s.gotenbergContainer, "3000")
+	if err != nil {
+		return fmt.Errorf("get container HTTP endpoint: %w", err)
+	}
+
+	record := func(resp *http.Response) (*httptest.ResponseRecorder, error) {
+		defer resp.Body.Close()
+
+		body, readErr := io.ReadAll(resp.Body)
+		if readErr != nil {
+			return nil, fmt.Errorf("read response body: %w", readErr)
+		}
+
+		rec := httptest.NewRecorder()
+		rec.Code = resp.StatusCode
+		for key, values := range resp.Header {
+			for _, v := range values {
+				rec.Header().Add(key, v)
+			}
+		}
+		_, writeErr := rec.Body.Write(body)
+		if writeErr != nil {
+			return nil, fmt.Errorf("write response body: %w", writeErr)
+		}
+
+		return rec, nil
+	}
+
+	s.probeResps = make([]*httptest.ResponseRecorder, 0, count)
+	s.sequentialResps = make([]*httptest.ResponseRecorder, 0, count)
+
+	for i := range count {
+		resp, reqErr := doFormDataRequest(method, fmt.Sprintf("%s%s", base, endpoint), fields, files, headers)
+		if reqErr != nil {
+			return fmt.Errorf("request %d: do request: %w", i+1, reqErr)
+		}
+
+		rec, recErr := record(resp)
+		if recErr != nil {
+			return fmt.Errorf("request %d: %w", i+1, recErr)
+		}
+		s.resp = rec
+		s.sequentialResps = append(s.sequentialResps, rec)
+
+		probeResp, probeErr := doRequest(http.MethodGet, fmt.Sprintf("%s%s", base, probeEndpoint), nil, nil)
+		if probeErr != nil {
+			return fmt.Errorf("probe %d: do request: %w", i+1, probeErr)
+		}
+
+		probeRec, probeRecErr := record(probeResp)
+		if probeRecErr != nil {
+			return fmt.Errorf("probe %d: %w", i+1, probeRecErr)
+		}
+		s.probeResps = append(s.probeResps, probeRec)
+	}
+
+	return nil
+}
+
+func (s *scenario) allProbeResponseStatusCodesShouldBe(expected int) error {
+	if len(s.probeResps) == 0 {
+		return errors.New("no probe responses recorded")
+	}
+
+	for i, resp := range s.probeResps {
+		if resp.Code != expected {
+			return fmt.Errorf("probe %d: expected status %d, got %d %q", i+1, expected, resp.Code, resp.Body.String())
+		}
+	}
+
+	return nil
+}
+
+func (s *scenario) allSequentialResponseStatusCodesShouldBe(expected int) error {
+	if len(s.sequentialResps) == 0 {
+		return errors.New("no sequential responses recorded")
+	}
+
+	for i, resp := range s.sequentialResps {
+		if resp.Code != expected {
+			return fmt.Errorf("sequential response %d: expected status %d, got %d %q", i+1, expected, resp.Code, resp.Body.String())
+		}
+	}
+
+	return nil
+}
+
 func (s *scenario) allConcurrentResponseStatusCodesShouldBe(expected int) error {
 	if len(s.concurrentResps) == 0 {
 		return errors.New("no concurrent responses recorded")
@@ -1644,10 +1769,13 @@ func InitializeScenario(ctx *godog.ScenarioContext) {
 	ctx.When(`^I make a "(GET|HEAD)" request to Gotenberg at the "([^"]*)" endpoint with the following header\(s\):$`, s.iMakeARequestToGotenbergWithTheFollowingHeaders)
 	ctx.When(`^I make a "(POST)" request to Gotenberg at the "([^"]*)" endpoint with the following form data and header\(s\):$`, s.iMakeARequestToGotenbergWithTheFollowingFormDataAndHeaders)
 	ctx.When(`^I make (\d+) concurrent "(POST)" requests to Gotenberg at the "([^"]*)" endpoint with the following form data and header\(s\):$`, s.iMakeConcurrentRequestsToGotenberg)
+	ctx.When(`^I make (\d+) sequential "(POST)" requests to Gotenberg at the "([^"]*)" endpoint, probing "([^"]*)" after each, with the following form data and header\(s\):$`, s.iMakeSequentialRequestsToGotenbergProbing)
 	ctx.When(`^I wait for the asynchronous request to the webhook$`, s.iWaitForTheAsynchronousRequestToWebhook)
 	ctx.Then(`^the Gotenberg container (should|should NOT) log the following entries:$`, s.theGotenbergContainerShouldLogTheFollowingEntries)
 	ctx.Then(`^the response status code should be (\d+)$`, s.theResponseStatusCodeShouldBe)
 	ctx.Then(`^all concurrent response status codes should be (\d+)$`, s.allConcurrentResponseStatusCodesShouldBe)
+	ctx.Then(`^all probe response status codes should be (\d+)$`, s.allProbeResponseStatusCodesShouldBe)
+	ctx.Then(`^all sequential response status codes should be (\d+)$`, s.allSequentialResponseStatusCodesShouldBe)
 	ctx.Then(`^all concurrent responses should have (\d+) PDF\(s\)$`, s.allConcurrentResponsesShouldHavePdfs)
 	ctx.Then(`^the (response|webhook request|file request|server request) header "([^"]*)" should be "([^"]*)"$`, s.theHeaderValueShouldBe)
 	ctx.Then(`^the webhook request header "([^"]*)" should carry trace id "([^"]*)"$`, s.theWebhookRequestHeaderShouldCarryTraceID)
@@ -1681,12 +1809,6 @@ func InitializeScenario(ctx *godog.ScenarioContext) {
 				return ctx, fmt.Errorf("terminate Gotenberg container: %w", errTerminate)
 			}
 		}
-		if s.gotenbergContainerNetwork != nil {
-			errRemove := s.gotenbergContainerNetwork.Remove(ctx)
-			if errRemove != nil {
-				return ctx, fmt.Errorf("remove Gotenberg container network: %w", errRemove)
-			}
-		}
 		return ctx, nil
 	})
 	ctx.After(func(ctx context.Context, sc *godog.Scenario, err error) (context.Context, error) {

test/integration/scenario/server.go

@@ -15,7 +15,7 @@ import (
 
 	"github.com/cucumber/godog"
 	"github.com/google/uuid"
-	"github.com/labstack/echo/v4"
+	"github.com/labstack/echo/v5"
 	"github.com/mholt/archives"
 )
 
@@ -26,12 +26,17 @@ type server struct {
 	errChan   chan error
 	eventBody []byte
 	eventMu   sync.Mutex
+
+	shutdown context.CancelFunc
+	done     chan struct{}
 }
 
 func newServer(ctx context.Context, workdir string) (*server, error) {
 	srv := echo.New()
-	srv.HideBanner = true
-	srv.HidePort = true
+	// The static file handlers below serve absolute paths, which Echo v5's
+	// default working-directory filesystem rejects. See newEchoServer in
+	// pkg/modules/api.
+	srv.Filesystem = echo.NewDefaultFS("/")
 	s := &server{
 		srv:     srv,
 		errChan: make(chan error, 1),
@@ -47,7 +52,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 		return err
 	}
 
-	webhookHandler := func(c echo.Context) error {
+	webhookHandler := func(c *echo.Context) error {
 		s.req = c.Request()
 
 		body, err := io.ReadAll(s.req.Body)
@@ -131,7 +136,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 
 		return webhookErr(c.String(http.StatusOK, http.StatusText(http.StatusOK)))
 	}
-	webhookErrorHandler := func(c echo.Context) error {
+	webhookErrorHandler := func(c *echo.Context) error {
 		s.req = c.Request()
 		body, err := io.ReadAll(s.req.Body)
 		if err != nil {
@@ -148,7 +153,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 	srv.PATCH("/webhook/error", webhookErrorHandler)
 	srv.PUT("/webhook/error", webhookErrorHandler)
 
-	webhookEventsHandler := func(c echo.Context) error {
+	webhookEventsHandler := func(c *echo.Context) error {
 		body, err := io.ReadAll(c.Request().Body)
 		if err != nil {
 			return c.String(http.StatusInternalServerError, err.Error())
@@ -159,7 +164,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 		return c.String(http.StatusOK, http.StatusText(http.StatusOK))
 	}
 	srv.POST("/webhook/events", webhookEventsHandler)
-	srv.GET("/static/:path", func(c echo.Context) error {
+	srv.GET("/static/:path", func(c *echo.Context) error {
 		s.req = c.Request()
 		path := c.Param("path")
 		if strings.Contains(path, "teststore") {
@@ -167,7 +172,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 		}
 		return c.Attachment(fmt.Sprintf("%s/%s", wd, path), filepath.Base(path))
 	})
-	srv.GET("/html/:path", func(c echo.Context) error {
+	srv.GET("/html/:path", func(c *echo.Context) error {
 		s.req = c.Request()
 		path := fmt.Sprintf("%s/%s", wd, c.Param("path"))
 		f, err := os.Open(path)
@@ -181,7 +186,7 @@ func newServer(ctx context.Context, workdir string) (*server, error) {
 		}
 		return c.HTML(http.StatusOK, string(b))
 	})
-	srv.GET("/redirect-to-private", func(c echo.Context) error {
+	srv.GET("/redirect-to-private", func(c *echo.Context) error {
 		s.req = c.Request()
 		// Redirect the browser to a non-public address so the outbound filter
 		// is exercised on the redirected request rather than on this URL.
@@ -206,9 +211,20 @@ func (s *server) start(ctx context.Context) (int, error) {
 
 	port := ln.Addr().(*net.TCPAddr).Port
 
+	startConfig := echo.StartConfig{
+		Listener:   ln,
+		HideBanner: true,
+		HidePort:   true,
+	}
+
+	serveCtx, cancel := context.WithCancel(context.Background())
+	s.shutdown = cancel
+	s.done = make(chan struct{})
+
 	go func() {
-		s.srv.Listener = ln
-		err = s.srv.Start("")
+		defer close(s.done)
+
+		err := startConfig.Start(serveCtx, s.srv)
 		if err != nil && !errors.Is(err, http.ErrServerClosed) {
 			godog.Log(ctx, err.Error())
 		}
@@ -219,5 +235,17 @@ func (s *server) start(ctx context.Context) (int, error) {
 
 func (s *server) stop(ctx context.Context) error {
 	close(s.errChan)
-	return s.srv.Shutdown(ctx)
+
+	if s.shutdown == nil {
+		return nil
+	}
+
+	s.shutdown()
+
+	select {
+	case <-s.done:
+		return nil
+	case <-ctx.Done():
+		return ctx.Err()
+	}
 }