diff --git a/e2e/utils/billing.ts b/e2e/utils/billing.ts
new file mode 100644
index 00000000..ecadb90f
--- /dev/null
+++ b/e2e/utils/billing.ts
@@ -0,0 +1,14 @@
+import { expect } from '@playwright/test';
+import { PLAYWRIGHT_BASE_URL } from '../../playwright/config';
+import type { TestContext } from './api';
+
+/**
+ * End the trial of the test organization, only works with the Billing extension. Reload the page
+ * afterwards, the page props still contain the trial otherwise.
+ */
+export async function cancelTrialViaApi(ctx: TestContext): Promise<void> {
+    const response = await ctx.request.post(
+        `${PLAYWRIGHT_BASE_URL}/api/v1/organizations/${ctx.orgId}/trial/cancel`
+    );
+    expect(response.status()).toBe(204);
+}
diff --git a/playwright.config.ts b/playwright.config.ts
index cfb92834..945e4c8d 100644
--- a/playwright.config.ts
+++ b/playwright.config.ts
@@ -1,5 +1,5 @@
 import { defineConfig, devices } from '@playwright/test';
-import { existsSync, readFileSync } from 'node:fs';
+import { enabledExtensions } from './playwright/config';
 
 /**
  * Read environment variables from file.
@@ -7,23 +7,11 @@ import { existsSync, readFileSync } from 'node:fs';
  */
 // require('dotenv').config();
 
-/**
+/*
  * Extensions ship their e2e specs in extensions/<Name>/tests/e2e. Only the specs of extensions
  * that are enabled in modules_statuses.json (php artisan module:enable <Name>) are collected,
  * a checked out but disabled extension would fail its specs otherwise.
- */
-function enabledExtensions(): string[] {
-    const statusesFile = './modules_statuses.json';
-    if (!existsSync(statusesFile)) {
-        return [];
-    }
-    const statuses: Record<string, boolean> = JSON.parse(readFileSync(statusesFile, 'utf-8'));
-    return Object.entries(statuses)
-        .filter(([, enabled]) => enabled)
-        .map(([name]) => name);
-}
-
-/*
+ *
  * Every test root gets its own testDir (instead of testDir: '.') so playwright does not walk the
  * whole repository, including node_modules, vendor and nested worktrees, to find the specs.
  */
diff --git a/playwright/config.ts b/playwright/config.ts
index 69783876..f5633c55 100644
--- a/playwright/config.ts
+++ b/playwright/config.ts
@@ -1,3 +1,23 @@
+import { existsSync, readFileSync } from 'node:fs';
+
 export const PLAYWRIGHT_BASE_URL = process.env.PLAYWRIGHT_BASE_URL ?? 'http://solidtime.test';
 export const MAILPIT_BASE_URL = process.env.MAILPIT_BASE_URL ?? 'http://mailpit:8025';
 export const TEST_USER_PASSWORD = 'amazingpassword123';
+
+/**
+ * Extensions that are enabled in modules_statuses.json (php artisan module:enable <Name>)
+ */
+export function enabledExtensions(): string[] {
+    const statusesFile = './modules_statuses.json';
+    if (!existsSync(statusesFile)) {
+        return [];
+    }
+    const statuses: Record<string, boolean> = JSON.parse(readFileSync(statusesFile, 'utf-8'));
+    return Object.entries(statuses)
+        .filter(([, enabled]) => enabled)
+        .map(([name]) => name);
+}
+
+export function isExtensionEnabled(name: string): boolean {
+    return enabledExtensions().includes(name);
+}
diff --git a/resources/js/Components/Billing/BillingBanner.vue b/resources/js/Components/Billing/BillingBanner.vue
index 4f23784f..fe40cc9e 100644
--- a/resources/js/Components/Billing/BillingBanner.vue
+++ b/resources/js/Components/Billing/BillingBanner.vue
@@ -1,137 +1,21 @@
 <script setup lang="ts">
 import MainContainer from '@/packages/ui/src/MainContainer.vue';
-import { CheckBadgeIcon, XMarkIcon, XCircleIcon } from '@heroicons/vue/16/solid';
+import { XMarkIcon, XCircleIcon } from '@heroicons/vue/16/solid';
 import { Link } from '@inertiajs/vue3';
 import { computed } from 'vue';
-import {
-    daysLeftInTrial,
-    isBillingActivated,
-    isBlocked,
-    isFreePlan,
-    isInTrial,
-} from '@/utils/billing';
+import { isBillingActivated, isBlocked } from '@/utils/billing';
 import { useSessionStorage } from '@vueuse/core';
 import { getCurrentOrganizationId } from '@/utils/useUser';
 import { canManageBilling } from '@/utils/permissions';
 
-const hideTrialBanner = useSessionStorage('showTrialBanner-' + getCurrentOrganizationId(), false);
-const showTrialBanner = computed(() => isInTrial() && !hideTrialBanner.value);
 const hideBlockedBanner = useSessionStorage(
     'showBlockedBanner-' + getCurrentOrganizationId(),
     false
 );
 const showBlockedBanner = computed(() => isBlocked() && !hideBlockedBanner.value);
-const hideFreeUpgradeBanner = useSessionStorage(
-    'showFreeUpgradeBanner-' + getCurrentOrganizationId(),
-    false
-);
-const showFreeUpgradeBanner = computed(
-    () =>
-        isFreePlan() && !isBlocked() && !hideFreeUpgradeBanner.value && !showBlackFridayBanner.value
-);
-const hideBlackFridayBanner = useSessionStorage(
-    'hideBlackFridayBanner-' + getCurrentOrganizationId(),
-    false
-);
-
-const showBlackFridayBanner = computed(() => {
-    if (hideBlackFridayBanner.value) {
-        return false;
-    }
-    const today = new Date();
-    const blackFriday = new Date(2024, 10, 30);
-    return today < blackFriday;
-});
 </script>
 
 <template>
-    <div
-        v-if="showBlackFridayBanner"
-        class="bg-tertiary text-xs lg:text-sm pb-1 pt-2 border-b border-border-secondary">
-        <MainContainer class="flex items-center justify-between">
-            <div class="flex items-center space-x-1.5">
-                <svg class="w-4 mr-1" viewBox="0 0 256 256" xmlns="http://www.w3.org/2000/svg">
-                    <path
-                        fill="#FF37AD"
-                        d="M22.498 68.97a11.845 11.845 0 1 0 0-23.687c-6.471.098-11.666 5.372-11.666 11.844s5.195 11.746 11.666 11.844m181.393-10.04a11.845 11.845 0 1 0-.003-23.688c-6.471.098-11.665 5.373-11.665 11.845c.001 6.472 5.197 11.745 11.668 11.842" />
-                    <path
-                        fill="#FCC954"
-                        d="M213.503 211.097a11.845 11.845 0 1 0-.003-23.687c-6.471.098-11.665 5.373-11.664 11.845s5.196 11.745 11.667 11.842M70.872 23.689a11.845 11.845 0 1 0 0-23.688C64.4.1 59.206 5.373 59.206 11.845S64.4 23.591 70.872 23.689" />
-                    <path
-                        fill="#2890E9"
-                        d="M140.945 105.94a9.25 9.25 0 0 1-8.974-11.484c.37-1.482.672-2.97.899-4.455a25.4 25.4 0 0 1-8.732 1.904c-5.379.205-10.195-.702-14.3-2.69a22.23 22.23 0 0 1-9.614-8.877c-4.415-7.652-4.034-17.718.964-25.645c4.765-7.568 12.836-11.664 21.586-10.995c6.74.527 12.647 3.051 17.378 7.382q1.293-3.647 2.473-7.803c4.833-17.058 6.429-34.187 6.442-34.36a9.24 9.24 0 0 1 10.041-8.37a9.25 9.25 0 0 1 8.37 10.044c-.067.767-1.768 19.03-7.068 37.735c-2.676 9.445-5.838 17.426-9.42 23.798q.396 2.13.631 4.372c.746 7.211.152 14.974-1.714 22.445a9.256 9.256 0 0 1-8.962 6.998m-20.123-43.827c-.956 0-2.64.28-3.996 2.43c-1.298 2.06-1.552 4.873-.588 6.544c1.282 2.223 5.054 2.417 7.19 2.336c2.424-.092 4.908-1.612 7.338-4.382a16 16 0 0 0-1.43-2.422c-2.007-2.787-4.547-4.212-7.998-4.482c-.13-.008-.305-.024-.516-.024" />
-                    <path
-                        fill="#F0A420"
-                        d="M114.361 131.268c-38.343-30.224-78.42-43.319-89.514-29.246a12.8 12.8 0 0 0-2.257 4.509a4 4 0 0 0-.156.61v.024q-.223.947-.333 1.917L.393 236.18c-3.477 20.412 16.73 36.755 35.967 29.093l117.721-46.908c2.076-.826 7.185-3.982 8.583-5.724q.556-.544 1.037-1.153c11.092-14.075-11-49.988-49.34-80.223z" />
-                    <path
-                        fill="#FCC954"
-                        d="M163.688 211.494c11.1-14.08-10.984-50-49.327-80.226c-38.343-30.227-78.425-43.316-89.524-29.236s10.983 50 49.326 80.226c38.343 30.227 78.425 43.316 89.525 29.236" />
-                    <path
-                        fill="#F0A420"
-                        d="M156.994 203.294c9.108-11.556-10.956-42.563-44.817-69.256c-33.861-26.695-68.697-38.966-77.804-27.413c-9.11 11.556 10.954 42.563 44.815 69.256c33.86 26.695 68.697 38.969 77.806 27.413" />
-                    <path
-                        fill="#2E6AC9"
-                        d="M76.059 249.456c-14.327.07-26.004-7.101-40.158-18.257C19.431 218.21 8.493 202.665 7.63 193.81l-4.668 27.327c2.16 7.798 9.523 17.683 20.202 26.101c8.883 7.004 17.844 11.813 27.135 12.48l25.76-10.266zm-14.332-49.6c-27.443-21.637-45.271-46.467-44.77-60.669l-4.549 26.63c.351 12.685 15.175 33.184 36.262 49.808c18.894 14.896 38.583 25.38 53.66 23.363l25.593-10.2c-20.62 1.425-42.376-10.147-66.196-28.931" />
-                    <path
-                        fill="#2890E9"
-                        d="M118.535 145.052a11.845 11.845 0 1 0 0-23.688c-6.471.098-11.666 5.372-11.666 11.844s5.195 11.746 11.666 11.844" />
-                    <path
-                        fill="#FF37AD"
-                        d="m182.412 122.007l.087-.097c.108-.116.308-.33.596-.621a45 45 0 0 1 2.8-2.56c3.56-2.98 7.45-5.54 11.594-7.63c10.128-5.125 25.208-9.307 44.985-4.747c5.943 1.37 11.87-2.336 13.241-8.278c1.37-5.942-2.336-11.87-8.278-13.24c-25.602-5.903-45.957-.506-59.922 6.566a82.5 82.5 0 0 0-15.857 10.449a66 66 0 0 0-4.215 3.866a45 45 0 0 0-1.53 1.615l-.12.135l-.042.048l-.02.022l-.007.008c-.003.005-.009.01 8.361 7.21l-8.37-7.2c-3.877 4.622-3.328 11.5 1.233 15.448s11.446 3.506 15.464-.994M73.03 43.248a11.75 11.75 0 0 0-16.23-3.664a11.76 11.76 0 0 0-3.665 16.227c.427.683 9.178 14.86 10.976 34.276c1.83 19.727-3.966 37.86-17.253 54.12c4.474 5.686 9.858 11.596 16.008 17.507c8.51-9.834 14.913-20.402 19.12-31.583c5.175-13.756 7.006-28.342 5.445-43.348c-2.487-23.874-12.874-41.11-14.402-43.535" />
-                    <path
-                        fill="#2890E9"
-                        d="M220.242 156.578c6.002 1.553 10.244 3.246 12.077 4.034a11.86 11.86 0 0 0 13.94-1.12a11.87 11.87 0 0 0 4.107-8.765a11.85 11.85 0 0 0-8.06-11.426c-5.618-2.495-26.905-10.92-55.044-9.423c-18.941 1.007-37.155 6.253-54.133 15.608c-16.076 8.86-31.004 21.412-44.556 37.425a199 199 0 0 0 20.17 12.607c22.882-26.08 49.283-40.217 78.7-42.085a105.9 105.9 0 0 1 32.8 3.145" />
-                </svg>
-                <div class="flex-1 space-x-1">
-                    <span class="font-medium">
-                        <strong>BLACK FRIDAY SALE!</strong> Use the code
-                        <strong>BLACKFRIDAY</strong> at checkout and get
-                        <strong>30% off</strong> the solidtime yearly plan.
-                    </span>
-                </div>
-            </div>
-            <div class="flex items-center space-x-2">
-                <Link v-if="canManageBilling()" href="/billing">
-                    <div
-                        class="text-text-primary font-semibold uppercase text-xs flex space-x-1 items-center hover:bg-white/10 rounded-lg px-2 py-1.5">
-                        <span>Upgrade now</span>
-                    </div>
-                </Link>
-                <button class="p-1" @click="hideBlackFridayBanner = true">
-                    <XMarkIcon class="w-4 opacity-50 hover:opacity-100"></XMarkIcon>
-                </button>
-            </div>
-        </MainContainer>
-    </div>
-    <div
-        v-if="showTrialBanner"
-        class="bg-accent-600/50 text-xs lg:text-sm py-0.5 border-b border-border-secondary">
-        <MainContainer class="flex items-center justify-between">
-            <div class="flex items-center space-x-1.5">
-                <CheckBadgeIcon class="w-4 text-text-primary/50"></CheckBadgeIcon>
-                <div class="flex-1 space-x-1">
-                    <span class="font-medium">
-                        Your trial expires in {{ daysLeftInTrial() }} days.
-                    </span>
-                    <span class="hidden md:inline">
-                        To continue using all features & support the development of solidtime,
-                        please upgrade your plan.
-                    </span>
-                </div>
-            </div>
-            <div class="flex items-center space-x-2">
-                <Link v-if="canManageBilling()" href="/billing">
-                    <div
-                        class="text-text-primary font-semibold uppercase text-xs flex space-x-1 items-center hover:bg-white/10 rounded-lg px-2 py-1.5">
-                        <span>Upgrade now</span>
-                    </div>
-                </Link>
-                <button class="p-1" @click="hideTrialBanner = true">
-                    <XMarkIcon class="w-4 opacity-50 hover:opacity-100"></XMarkIcon>
-                </button>
-            </div>
-        </MainContainer>
-    </div>
     <div
         v-if="showBlockedBanner"
         class="bg-red-600/50 text-xs lg:text-sm py-0.5 border-b border-border-secondary">
@@ -159,33 +43,6 @@ const showBlackFridayBanner = computed(() => {
             </div>
         </MainContainer>
     </div>
-    <div
-        v-if="showFreeUpgradeBanner"
-        class="bg-tertiary text-xs lg:text-sm py-0.5 border-b border-border-secondary">
-        <MainContainer class="flex items-center justify-between">
-            <div class="flex items-center space-x-1.5">
-                <XCircleIcon class="w-4 text-text-primary/50"></XCircleIcon>
-                <div class="flex-1 space-x-1">
-                    <span class="font-medium"> You are currently using the Free Plan. </span>
-                    <span class="hidden md:inline">
-                        To unlock all premium features & support the development of solidtime,
-                        please upgrade your plan.</span
-                    >
-                </div>
-            </div>
-            <div class="flex items-center space-x-2">
-                <Link v-if="isBillingActivated() && canManageBilling()" href="/billing">
-                    <div
-                        class="text-text-primary font-semibold uppercase text-xs flex space-x-1 items-center hover:bg-white/10 rounded-lg px-2 py-1.5">
-                        <span>Upgrade now</span>
-                    </div>
-                </Link>
-                <button class="p-1" @click="hideFreeUpgradeBanner = true">
-                    <XMarkIcon class="w-4 opacity-50 hover:opacity-100"></XMarkIcon>
-                </button>
-            </div>
-        </MainContainer>
-    </div>
 </template>
 
 <style scoped></style>
diff --git a/resources/js/Components/Billing/CancelTrialModal.vue b/resources/js/Components/Billing/CancelTrialModal.vue
new file mode 100644
index 00000000..1bd3e1bd
--- /dev/null
+++ b/resources/js/Components/Billing/CancelTrialModal.vue
@@ -0,0 +1,86 @@
+<script setup lang="ts">
+import { ref } from 'vue';
+import { router } from '@inertiajs/vue3';
+import DialogModal from '@/packages/ui/src/DialogModal.vue';
+import DangerButton from '@/packages/ui/src/Buttons/DangerButton.vue';
+import SecondaryButton from '@/packages/ui/src/Buttons/SecondaryButton.vue';
+import { XMarkIcon } from '@heroicons/vue/16/solid';
+import { useNotificationsStore } from '@/utils/notification';
+import { getCurrentOrganizationId } from '@/utils/useUser';
+import { api } from '@/packages/api/src';
+
+const show = defineModel<boolean>('show', { default: false });
+
+const processing = ref(false);
+const { handleApiRequestNotifications } = useNotificationsStore();
+
+const lostFeatures = [
+    'Billable hours & rates',
+    'Invoicing',
+    'Project & task estimates',
+    'Rounding of time entries',
+    'PDF reports & shareable reports',
+    'Team support & access management',
+];
+
+async function cancelTrial() {
+    // Note: The organization of this page, the current organization on the server can differ if the user switched organizations in another tab
+    const organizationId = getCurrentOrganizationId();
+    if (processing.value || organizationId === null) {
+        return;
+    }
+    processing.value = true;
+    try {
+        await handleApiRequestNotifications(
+            () => api.cancelTrial(undefined, { params: { organization: organizationId } }),
+            'Your trial has been canceled',
+            'Your trial could not be canceled, please try again',
+            () => {
+                show.value = false;
+                // Reloads the shared billing props of the page, they still contain the trial otherwise
+                router.reload();
+            }
+        );
+    } finally {
+        processing.value = false;
+    }
+}
+</script>
+
+<template>
+    <DialogModal :show="show" closeable @close="show = false">
+        <template #title>Cancel trial</template>
+
+        <template #content>
+            <p class="text-sm text-text-secondary">
+                Your organization switches to the Free plan right away. You will lose access to
+                these Professional features:
+            </p>
+            <ul class="mt-4 grid gap-2 sm:grid-cols-2">
+                <li
+                    v-for="feature in lostFeatures"
+                    :key="feature"
+                    class="flex items-center gap-2 text-sm text-text-primary">
+                    <XMarkIcon class="h-4 w-4 shrink-0 text-red-500/80" />
+                    {{ feature }}
+                </li>
+            </ul>
+            <p class="mt-5 text-sm text-text-secondary">
+                Organizations with more than one member are blocked until you upgrade or remove
+                everyone except the owner.
+            </p>
+        </template>
+
+        <template #footer>
+            <SecondaryButton @click="show = false">Keep trial</SecondaryButton>
+            <DangerButton
+                class="ms-3"
+                data-testid="confirm_cancel_trial"
+                :class="{ 'opacity-25': processing }"
+                :disabled="processing"
+                @click="cancelTrial">
+                Cancel trial
+            </DangerButton>
+        </template>
+    </DialogModal>
+</template>
diff --git a/resources/js/Components/Billing/SidebarPlanStatus.vue b/resources/js/Components/Billing/SidebarPlanStatus.vue
new file mode 100644
index 00000000..4115666d
--- /dev/null
+++ b/resources/js/Components/Billing/SidebarPlanStatus.vue
@@ -0,0 +1,56 @@
+<script setup lang="ts">
+import { computed, ref } from 'vue';
+import { router } from '@inertiajs/vue3';
+import { SparklesIcon } from '@heroicons/vue/16/solid';
+import { Button } from '@/packages/ui/src/Buttons';
+import TrialUpgradeModal from '@/Components/Billing/TrialUpgradeModal.vue';
+import CancelTrialModal from '@/Components/Billing/CancelTrialModal.vue';
+import { daysLeftInTrial, isBlocked, isFreePlan, isInTrial } from '@/utils/billing';
+
+const showTrialUpgradeModal = ref(false);
+const showCancelTrialModal = ref(false);
+
+const daysLeftLabel = computed(() => {
+    const days = daysLeftInTrial();
+    return days === 1 ? '1 day left' : `${days} days left`;
+});
+
+function openBilling() {
+    router.visit('/billing');
+}
+</script>
+
+<template>
+    <div v-if="isInTrial() || (isFreePlan() && !isBlocked())" class="pb-3">
+        <Button
+            v-if="isInTrial()"
+            variant="outline"
+            size="sm"
+            data-testid="sidebar_trial_days_left"
+            class="w-full justify-between rounded-lg px-2.5 text-xs font-normal [&_svg]:size-3.5"
+            @click="showTrialUpgradeModal = true">
+            <span class="flex items-center gap-1.5 font-medium text-text-primary">
+                <SparklesIcon class="h-3.5 w-3.5 text-accent-500 dark:text-accent-300" />
+                Professional trial
+            </span>
+            <span class="text-text-secondary">{{ daysLeftLabel }}</span>
+        </Button>
+        <div
+            v-else-if="isFreePlan() && !isBlocked()"
+            class="flex items-center justify-between gap-2 rounded-lg border border-border-secondary bg-card-background py-1.5 pl-2.5 pr-1.5 text-xs">
+            <span class="font-medium text-text-primary">Free plan</span>
+            <Button
+                size="xs"
+                data-testid="sidebar_upgrade_button"
+                class="h-6 bg-accent-500 px-2.5 font-semibold text-white hover:bg-accent-400"
+                @click="openBilling">
+                Upgrade
+            </Button>
+        </div>
+
+        <TrialUpgradeModal
+            v-model:show="showTrialUpgradeModal"
+            @cancel-trial="showCancelTrialModal = true" />
+        <CancelTrialModal v-model:show="showCancelTrialModal" />
+    </div>
+</template>
diff --git a/resources/js/Components/Billing/TrialUpgradeModal.vue b/resources/js/Components/Billing/TrialUpgradeModal.vue
new file mode 100644
index 00000000..39716075
--- /dev/null
+++ b/resources/js/Components/Billing/TrialUpgradeModal.vue
@@ -0,0 +1,79 @@
+<script setup lang="ts">
+import { computed } from 'vue';
+import { Dialog, DialogContent, DialogTitle, DialogDescription } from '@/packages/ui/src/dialog';
+import { Button } from '@/packages/ui/src/Buttons';
+import { SparklesIcon } from '@heroicons/vue/16/solid';
+import { featureIcons } from '@/packages/ui/src/UpgradeModal/featureIcons';
+import { professionalFeatures, useUpgradeCta } from '@/packages/ui/src/UpgradeModal/useUpgradeCta';
+import { daysLeftInTrial } from '@/utils/billing';
+
+const show = defineModel<boolean>('show', { default: false });
+
+const emit = defineEmits<{ cancelTrial: [] }>();
+
+const { goToBilling } = useUpgradeCta();
+
+const daysLeftLabel = computed(() => {
+    const days = daysLeftInTrial();
+    return days === 1 ? '1 day' : `${days} days`;
+});
+
+function cancelTrial() {
+    show.value = false;
+    emit('cancelTrial');
+}
+</script>
+
+<template>
+    <Dialog v-model:open="show">
+        <DialogContent class="sm:max-w-xl p-0 overflow-hidden">
+            <div class="px-8 pt-8 text-center">
+                <div
+                    class="mx-auto inline-flex items-center gap-1.5 rounded-full border border-border-secondary bg-card-background px-3 py-1 text-xs font-medium text-text-primary">
+                    <SparklesIcon class="h-3.5 w-3.5 text-accent-500 dark:text-accent-300" />
+                    {{ daysLeftLabel }} left in your trial
+                </div>
+                <DialogTitle class="mt-4 text-xl font-semibold tracking-tight text-text-primary">
+                    Keep solidtime Professional
+                </DialogTitle>
+                <DialogDescription class="mt-1.5 text-sm text-text-secondary">
+                    Upgrade now to keep these features after your trial ends.
+                </DialogDescription>
+            </div>
+
+            <div class="grid grid-cols-2 gap-x-6 gap-y-4 px-8 pt-8">
+                <div v-for="item in professionalFeatures" :key="item.key" class="flex gap-3">
+                    <div
+                        class="flex h-7 w-7 shrink-0 items-center justify-center rounded-md border border-border-tertiary bg-card-background">
+                        <component
+                            :is="featureIcons[item.key]"
+                            class="h-3.5 w-3.5 text-text-secondary" />
+                    </div>
+                    <div class="min-w-0">
+                        <p class="text-sm font-medium text-text-primary">{{ item.title }}</p>
+                        <p class="mt-0.5 text-xs leading-relaxed text-text-tertiary">
+                            {{ item.description }}
+                        </p>
+                    </div>
+                </div>
+            </div>
+
+            <div class="mx-auto flex max-w-xs flex-col items-center gap-3 px-8 pt-8 pb-6">
+                <Button
+                    data-testid="trial_upgrade_modal_cta"
+                    class="w-full bg-accent-500 px-4 font-semibold text-white shadow-[0_0_24px_-6px] shadow-accent-500/60 hover:bg-accent-400"
+                    @click="goToBilling">
+                    Upgrade to Professional
+                </Button>
+                <Button
+                    variant="ghost"
+                    size="xs"
+                    data-testid="trial_upgrade_modal_cancel_trial"
+                    class="font-normal text-text-tertiary hover:text-text-primary"
+                    @click="cancelTrial">
+                    Cancel trial
+                </Button>
+            </div>
+        </DialogContent>
+    </Dialog>
+</template>
diff --git a/resources/js/Components/Common/Project/ProjectTableRow.vue b/resources/js/Components/Common/Project/ProjectTableRow.vue
index 5be8d918..2a0164b2 100644
--- a/resources/js/Components/Common/Project/ProjectTableRow.vue
+++ b/resources/js/Components/Common/Project/ProjectTableRow.vue
@@ -18,7 +18,7 @@ import ProjectEditModal from '@/Components/Common/Project/ProjectEditModal.vue';
 import { formatCents } from '@/packages/ui/src/utils/money';
 import { getOrganizationCurrencyString } from '@/utils/money';
 import EstimatedTimeProgress from '@/packages/ui/src/EstimatedTimeProgress.vue';
-import UpgradeBadge from '@/Components/Common/UpgradeBadge.vue';
+import UpgradeBadge from '@/packages/ui/src/UpgradeBadge.vue';
 import { formatHumanReadableDuration } from '../../../packages/ui/src/utils/time';
 import { isAllowedToPerformPremiumAction } from '@/utils/billing';
 import { canUpdateProjects, canDeleteProjects } from '@/utils/permissions';
@@ -119,7 +119,9 @@ const showEditProjectModal = ref(false);
                     <div v-else class="text-text-tertiary">--</div>
                 </div>
                 <div class="whitespace-nowrap px-3 flex items-center text-sm text-text-primary">
-                    <UpgradeBadge v-if="!isAllowedToPerformPremiumAction()"></UpgradeBadge>
+                    <UpgradeBadge
+                        v-if="!isAllowedToPerformPremiumAction()"
+                        feature="estimates"></UpgradeBadge>
                     <EstimatedTimeProgress
                         v-else-if="project.estimated_time"
                         :estimated="project.estimated_time"
diff --git a/resources/js/Components/Common/Report/ReportSaveButton.vue b/resources/js/Components/Common/Report/ReportSaveButton.vue
index f4396cc7..2438f1c3 100644
--- a/resources/js/Components/Common/Report/ReportSaveButton.vue
+++ b/resources/js/Components/Common/Report/ReportSaveButton.vue
@@ -4,7 +4,7 @@ import ReportCreateModal from '@/Components/Common/Report/ReportCreateModal.vue'
 import { h, ref } from 'vue';
 import type { CreateReportBodyProperties } from '@/packages/api/src';
 import { isAllowedToPerformPremiumAction } from '@/utils/billing';
-import UpgradeModal from '@/Components/Common/UpgradeModal.vue';
+import UpgradeModal from '@/packages/ui/src/UpgradeModal.vue';
 import { canCreateReports } from '@/utils/permissions';
 defineProps<{
     reportProperties: CreateReportBodyProperties;
@@ -30,9 +30,7 @@ function onSaveReportClick() {
     <ReportCreateModal
         v-model:show="showCreateReportModal"
         :properties="reportProperties"></ReportCreateModal>
-    <UpgradeModal v-model:show="showPremiumModal">
-        <strong>Sharable Reports</strong> is only available in solidtime Professional.
-    </UpgradeModal>
+    <UpgradeModal v-model:show="showPremiumModal" feature="shareable-reports" />
     <SecondaryButton v-if="canCreateReports()" :icon="SaveIcon" @click="onSaveReportClick"
         >Save Report</SecondaryButton
     >
diff --git a/resources/js/Components/Common/Reporting/ReportingExportButton.vue b/resources/js/Components/Common/Reporting/ReportingExportButton.vue
index 310870e7..63a22964 100644
--- a/resources/js/Components/Common/Reporting/ReportingExportButton.vue
+++ b/resources/js/Components/Common/Reporting/ReportingExportButton.vue
@@ -10,7 +10,7 @@ import {
 import type { ExportFormat } from '@/types/reporting';
 import { ref } from 'vue';
 import { isAllowedToPerformPremiumAction } from '@/utils/billing';
-import UpgradeModal from '@/Components/Common/UpgradeModal.vue';
+import UpgradeModal from '@/packages/ui/src/UpgradeModal.vue';
 
 const props = defineProps<{
     download: (format: ExportFormat) => Promise<void>;
@@ -48,9 +48,7 @@ function triggerDownload(format: ExportFormat) {
             <DropdownMenuItem @click="triggerDownload('ods')"> Export as ODS </DropdownMenuItem>
         </DropdownMenuContent>
     </DropdownMenu>
-    <UpgradeModal v-model:show="showPremiumModal">
-        <strong>PDF Reports</strong> are only available in solidtime Professional.
-    </UpgradeModal>
+    <UpgradeModal v-model:show="showPremiumModal" feature="pdf-reports" />
 </template>
 
 <style scoped></style>
diff --git a/resources/js/Components/Common/Reporting/ReportingOverview.vue b/resources/js/Components/Common/Reporting/ReportingOverview.vue
index 4a1b0af1..227f82b8 100644
--- a/resources/js/Components/Common/Reporting/ReportingOverview.vue
+++ b/resources/js/Components/Common/Reporting/ReportingOverview.vue
@@ -30,7 +30,8 @@ import {
     DropdownMenuTrigger,
 } from '@/packages/ui/src';
 import ReportCreateModal from '@/Components/Common/Report/ReportCreateModal.vue';
-import UpgradeModal from '@/Components/Common/UpgradeModal.vue';
+import UpgradeModal from '@/packages/ui/src/UpgradeModal.vue';
+import type { UpgradeFeature } from '@/packages/ui/src/UpgradeModal/useUpgradeCta';
 import { canCreateReports } from '@/utils/permissions';
 import { isAllowedToPerformPremiumAction } from '@/utils/billing';
 import { computed, type ComputedRef, inject, ref, watch } from 'vue';
@@ -214,10 +215,13 @@ const showExportModal = ref(false);
 const exportUrl = ref<string | null>(null);
 const showCreateReportModal = ref(false);
 const showPremiumModal = ref(false);
+// Note: The premium modal is shared by the PDF export and saving a report
+const premiumFeature = ref<UpgradeFeature>('pdf-reports');
 const exportLoading = ref(false);
 
 function triggerExport(format: ExportFormat) {
     if (format === 'pdf' && !isAllowedToPerformPremiumAction()) {
+        premiumFeature.value = 'pdf-reports';
         showPremiumModal.value = true;
         return;
     }
@@ -231,6 +235,7 @@ function onSaveReportClick() {
     if (isAllowedToPerformPremiumAction()) {
         showCreateReportModal.value = true;
     } else {
+        premiumFeature.value = 'shareable-reports';
         showPremiumModal.value = true;
     }
 }
@@ -299,9 +304,7 @@ const tableData = computed(() => {
     <ReportCreateModal
         v-model:show="showCreateReportModal"
         :properties="reportProperties"></ReportCreateModal>
-    <UpgradeModal v-model:show="showPremiumModal">
-        This feature is only available in solidtime Professional.
-    </UpgradeModal>
+    <UpgradeModal v-model:show="showPremiumModal" :feature="premiumFeature" />
     <MainContainer
         class="h-14 sm:h-16 border-b border-default-background-separator flex flex-wrap gap-y-3 justify-between items-center">
         <div class="flex items-center space-x-3 sm:space-x-6">
diff --git a/resources/js/Components/Common/Task/TaskTableRow.vue b/resources/js/Components/Common/Task/TaskTableRow.vue
index 99c52a81..e8e62501 100644
--- a/resources/js/Components/Common/Task/TaskTableRow.vue
+++ b/resources/js/Components/Common/Task/TaskTableRow.vue
@@ -9,7 +9,7 @@ import TaskEditModal from '@/Components/Common/Task/TaskEditModal.vue';
 import { ref, inject, type ComputedRef } from 'vue';
 import { isAllowedToPerformPremiumAction } from '@/utils/billing';
 import EstimatedTimeProgress from '@/packages/ui/src/EstimatedTimeProgress.vue';
-import UpgradeBadge from '@/Components/Common/UpgradeBadge.vue';
+import UpgradeBadge from '@/packages/ui/src/UpgradeBadge.vue';
 import { formatHumanReadableDuration } from '../../../packages/ui/src/utils/time';
 import type { Organization } from '@/packages/api/src';
 
@@ -55,7 +55,9 @@ const showTaskEditModal = ref(false);
             <span v-else> -- </span>
         </div>
         <div class="whitespace-nowrap px-3 flex items-center text-sm text-text-secondary">
-            <UpgradeBadge v-if="!isAllowedToPerformPremiumAction()"></UpgradeBadge>
+            <UpgradeBadge
+                v-if="!isAllowedToPerformPremiumAction()"
+                feature="estimates"></UpgradeBadge>
             <EstimatedTimeProgress
                 v-else-if="task.estimated_time"
                 :estimated="task.estimated_time"
diff --git a/resources/js/Components/Common/UpgradeModal.vue b/resources/js/Components/Common/UpgradeModal.vue
deleted file mode 100644
index 514a9da0..00000000
--- a/resources/js/Components/Common/UpgradeModal.vue
+++ /dev/null
@@ -1,67 +0,0 @@
-<script setup lang="ts">
-import DialogModal from '@/packages/ui/src/DialogModal.vue';
-import PrimaryButton from '@/packages/ui/src/Buttons/PrimaryButton.vue';
-import { Link } from '@inertiajs/vue3';
-import { isBillingActivated } from '@/utils/billing';
-import { CreditCardIcon, UserGroupIcon } from '@heroicons/vue/20/solid';
-import { canManageBilling, canUpdateOrganization } from '@/utils/permissions';
-import { SecondaryButton } from '@/packages/ui/src';
-
-const show = defineModel('show', { default: false });
-</script>
-
-<template>
-    <DialogModal closeable :show="show" @close="show = false">
-        <template #title>
-            <div class="flex space-x-2">
-                <span> Upgrade Plan </span>
-            </div>
-        </template>
-
-        <template #content>
-            <div>
-                <div
-                    class="rounded-full flex items-center justify-center w-20 h-20 mx-auto border border-border-tertiary bg-secondary">
-                    <UserGroupIcon class="w-12"></UserGroupIcon>
-                </div>
-                <div class="max-w-sm text-center mx-auto py-4 text-base">
-                    <p class="py-1">
-                        <slot></slot>
-                    </p>
-                    <p class="py-1 text-sm">
-                        If you want to use this feature,
-                        <strong class="font-semibold text-text-primary"
-                            >please upgrade to a paid plan</strong
-                        >
-                        or
-                        <strong class="font-semibold text-text-primary"
-                            >request a free trial</strong
-                        >
-                        via
-                        <a
-                            class="text-accent-200/80 transition text-accent-300"
-                            href="mailto:hello@solidtime.io"
-                            >hello@solidtime.io</a
-                        >
-                        to try out this feature.
-                    </p>
-
-                    <Link v-if="isBillingActivated() && canManageBilling()" href="/billing">
-                        <PrimaryButton
-                            v-if="isBillingActivated() && canUpdateOrganization()"
-                            type="button"
-                            class="mt-6"
-                            :icon="CreditCardIcon">
-                            Go to Billing
-                        </PrimaryButton>
-                    </Link>
-                </div>
-            </div>
-        </template>
-        <template #footer>
-            <SecondaryButton @click="show = false">Close</SecondaryButton>
-        </template>
-    </DialogModal>
-</template>
-
-<style scoped></style>
diff --git a/resources/js/Layouts/AppLayout.vue b/resources/js/Layouts/AppLayout.vue
index 4bad78e2..9e869082 100644
--- a/resources/js/Layouts/AppLayout.vue
+++ b/resources/js/Layouts/AppLayout.vue
@@ -1,5 +1,5 @@
 <script setup lang="ts">
-import { Head, usePage } from '@inertiajs/vue3';
+import { Head, router, usePage } from '@inertiajs/vue3';
 import Banner from '@/Components/Banner.vue';
 import OrganizationSwitcher from '@/Components/OrganizationSwitcher.vue';
 import CurrentSidebarTimer from '@/Components/CurrentSidebarTimer.vue';
@@ -23,7 +23,7 @@ import { PanelLeft, Target } from '@lucide/vue';
 import NavigationSidebarItem from '@/Components/NavigationSidebarItem.vue';
 import UserSettingsIcon from '@/Components/UserSettingsIcon.vue';
 import MainContainer from '@/packages/ui/src/MainContainer.vue';
-import { nextTick, onMounted, provide, ref } from 'vue';
+import { computed, nextTick, onMounted, provide, ref } from 'vue';
 import NotificationContainer from '@/Components/NotificationContainer.vue';
 import { initializeStores } from '@/utils/init';
 import { useCurrentTimeEntryStore } from '@/utils/useCurrentTimeEntry';
@@ -39,11 +39,13 @@ import {
     canViewTags,
 } from '@/utils/permissions';
 import { isBillingActivated, isInvoicingActivated } from '@/utils/billing';
+import { upgradeCtaKey } from '@/packages/ui/src/UpgradeModal/useUpgradeCta';
 import type { User } from '@/types/models';
 import { ArrowsRightLeftIcon } from '@heroicons/vue/16/solid';
 import { fetchToken, isTokenValid } from '@/utils/session';
 import UpdateSidebarNotification from '@/Components/UpdateSidebarNotification.vue';
 import BillingBanner from '@/Components/Billing/BillingBanner.vue';
+import SidebarPlanStatus from '@/Components/Billing/SidebarPlanStatus.vue';
 import UserTimezoneMismatchModal from '@/Components/Common/User/UserTimezoneMismatchModal.vue';
 import { useTheme } from '@/utils/theme';
 import { useOrganizationQuery } from '@/utils/useOrganizationQuery';
@@ -89,6 +91,11 @@ const { organization, isLoading: isOrganizationLoading } = useOrganizationQuery(
 
 provide('organization', organization);
 
+provide(upgradeCtaKey, {
+    canUpgrade: computed(() => isBillingActivated() && canManageBilling()),
+    goToBilling: () => router.visit('/billing'),
+});
+
 onMounted(async () => {
     useTheme();
     // make sure that the initial requests are only loaded once, this can be removed once we move away from inertia
@@ -306,6 +313,7 @@ const page = usePage<{
                 </div>
                 <div class="justify-self-end">
                     <UpdateSidebarNotification></UpdateSidebarNotification>
+                    <SidebarPlanStatus v-if="isBillingActivated() && canManageBilling()" />
                     <ul
                         class="border-t border-default-background-separator pt-3 gap-1 flex justify-between items-center">
                         <UserSettingsIcon></UserSettingsIcon>
diff --git a/resources/js/Pages/Goals.vue b/resources/js/Pages/Goals.vue
index 982d4473..1b2bd8ff 100644
--- a/resources/js/Pages/Goals.vue
+++ b/resources/js/Pages/Goals.vue
@@ -8,9 +8,9 @@ import { computed, ref } from 'vue';
 import GoalTable from '@/Components/Common/Goal/GoalTable.vue';
 import GoalCreateModal from '@/Components/Common/Goal/GoalCreateModal.vue';
 import PageTitle from '@/Components/Common/PageTitle.vue';
-import UpgradeBadge from '@/Components/Common/UpgradeBadge.vue';
+import UpgradeBadge from '@/packages/ui/src/UpgradeBadge.vue';
 import { canCreateGoals } from '@/utils/permissions';
-import { canCreateMoreGoals, goalLimit } from '@/utils/billing';
+import { canCreateMoreGoals } from '@/utils/billing';
 import { useGoalsQuery } from '@/utils/useGoalsQuery';
 import { TabBar, TabBarItem } from '@/packages/ui/src';
 
@@ -25,7 +25,6 @@ const visibleGoals = computed(() =>
 );
 const archivedCount = computed(() => goals.value.filter((goal) => goal.is_archived).length);
 const canCreateMore = computed(() => canCreateMoreGoals(goals.value.length));
-const limit = goalLimit();
 </script>
 
 <template>
@@ -43,10 +42,7 @@ const limit = goalLimit();
                 </TabBar>
             </div>
             <div class="flex items-center space-x-3">
-                <UpgradeBadge v-if="canCreateGoals() && !canCreateMore">
-                    <strong>More than {{ limit }} goal{{ limit === 1 ? '' : 's' }}</strong> is only
-                    available in solidtime Professional.
-                </UpgradeBadge>
+                <UpgradeBadge v-if="canCreateGoals() && !canCreateMore" feature="goals" />
                 <SecondaryButton
                     v-if="canCreateGoals() && canCreateMore"
                     :icon="PlusIcon"
diff --git a/resources/js/Pages/ReportingDetailed.vue b/resources/js/Pages/ReportingDetailed.vue
index 004d25ae..f793d99f 100644
--- a/resources/js/Pages/ReportingDetailed.vue
+++ b/resources/js/Pages/ReportingDetailed.vue
@@ -43,7 +43,7 @@ import { useMembersQuery } from '@/utils/useMembersQuery';
 import { useQueryClient } from '@tanstack/vue-query';
 import { getCurrentOrganizationId, getCurrentMembershipId } from '@/utils/useUser';
 import ReportingTabNavbar from '@/Components/Common/Reporting/ReportingTabNavbar.vue';
-import UpgradeModal from '@/Components/Common/UpgradeModal.vue';
+import UpgradeModal from '@/packages/ui/src/UpgradeModal.vue';
 import type { ExportFormat } from '@/types/reporting';
 import { useNotificationsStore } from '@/utils/notification';
 import TimeEntryMassActionRow from '@/packages/ui/src/TimeEntry/TimeEntryMassActionRow.vue';
@@ -253,9 +253,7 @@ async function downloadExport(format: ExportFormat) {
         <ReportingExportModal
             v-model:show="showExportModal"
             :export-url="exportUrl"></ReportingExportModal>
-        <UpgradeModal v-model:show="showPremiumModal">
-            <strong>PDF Reports</strong> are only available in solidtime Professional.
-        </UpgradeModal>
+        <UpgradeModal v-model:show="showPremiumModal" feature="pdf-reports" />
         <MainContainer
             class="h-14 sm:h-16 border-b border-default-background-separator flex flex-wrap gap-y-3 justify-between items-center">
             <div class="flex items-center space-x-3 sm:space-x-6">
diff --git a/resources/js/Pages/Teams/Partials/OrganizationTrial.vue b/resources/js/Pages/Teams/Partials/OrganizationTrial.vue
new file mode 100644
index 00000000..786b23cd
--- /dev/null
+++ b/resources/js/Pages/Teams/Partials/OrganizationTrial.vue
@@ -0,0 +1,51 @@
+<script setup lang="ts">
+import { computed, inject, ref, type ComputedRef } from 'vue';
+import { usePage } from '@inertiajs/vue3';
+import ActionSection from '@/Components/ActionSection.vue';
+import SecondaryButton from '@/packages/ui/src/Buttons/SecondaryButton.vue';
+import CancelTrialModal from '@/Components/Billing/CancelTrialModal.vue';
+import { daysLeftInTrial } from '@/utils/billing';
+import { formatDateLocalized } from '@/packages/ui/src/utils/time';
+import type { Organization } from '@/packages/api/src';
+
+const showCancelTrialModal = ref(false);
+
+const organization = inject<ComputedRef<Organization | undefined>>('organization');
+const page = usePage<{ billing: { trial_until: string | null } | null }>();
+const trialUntil = computed(() =>
+    page.props.billing?.trial_until
+        ? formatDateLocalized(page.props.billing.trial_until, organization?.value?.date_format)
+        : null
+);
+const daysLeftLabel = computed(() => {
+    const days = daysLeftInTrial();
+    return days === 1 ? '1 day' : `${days} days`;
+});
+</script>
+
+<template>
+    <ActionSection>
+        <template #title>Trial</template>
+
+        <template #description>Your organization is trying out solidtime Professional.</template>
+
+        <template #content>
+            <div class="max-w-xl text-sm text-text-secondary">
+                Your trial ends in
+                <span class="font-medium text-text-primary">{{ daysLeftLabel }}</span>
+                <template v-if="trialUntil"> ({{ trialUntil }})</template>. If you don't need the
+                Professional features, you can switch to the Free plan right away.
+            </div>
+
+            <div class="mt-5">
+                <SecondaryButton
+                    data-testid="cancel_trial_button"
+                    @click="showCancelTrialModal = true">
+                    Cancel trial
+                </SecondaryButton>
+            </div>
+
+            <CancelTrialModal v-model:show="showCancelTrialModal" />
+        </template>
+    </ActionSection>
+</template>
diff --git a/resources/js/Pages/Teams/Show.vue b/resources/js/Pages/Teams/Show.vue
index 5c7d7316..4922c621 100644
--- a/resources/js/Pages/Teams/Show.vue
+++ b/resources/js/Pages/Teams/Show.vue
@@ -8,6 +8,9 @@ import type { Permissions } from '@/types/jetstream';
 import OrganizationBillableRate from '@/Pages/Teams/Partials/OrganizationBillableRate.vue';
 import OrganizationFormatSettings from '@/Pages/Teams/Partials/OrganizationFormatSettings.vue';
 import OrganizationTimeEntrySettings from '@/Pages/Teams/Partials/OrganizationTimeEntrySettings.vue';
+import OrganizationTrial from '@/Pages/Teams/Partials/OrganizationTrial.vue';
+import { isBillingActivated, isInTrial } from '@/utils/billing';
+import { canManageBilling } from '@/utils/permissions';
 import { onMounted, ref } from 'vue';
 import { useOrganizationStore } from '@/utils/useOrganization';
 import { storeToRefs } from 'pinia';
@@ -52,6 +55,11 @@ onMounted(async () => {
                     <SectionBorder v-if="permissions.canUpdateTeam" />
                     <OrganizationTimeEntrySettings v-if="permissions.canUpdateTeam" />
 
+                    <template v-if="isBillingActivated() && isInTrial() && canManageBilling()">
+                        <SectionBorder />
+                        <OrganizationTrial />
+                    </template>
+
                     <template v-if="permissions.canDeleteTeam">
                         <SectionBorder />
                         <DeleteTeamForm class="mt-10 sm:mt-0" :team="team" />
diff --git a/resources/js/packages/api/src/openapi.json.client.ts b/resources/js/packages/api/src/openapi.json.client.ts
index 89ea1594..de1b7d6b 100644
--- a/resources/js/packages/api/src/openapi.json.client.ts
+++ b/resources/js/packages/api/src/openapi.json.client.ts
@@ -5069,6 +5069,45 @@ If the group parameters are all set to &#x60;null&#x60; or are all missing, the
             },
         ],
     },
+    {
+        method: 'post',
+        path: '/v1/organizations/:organization/trial/cancel',
+        alias: 'cancelTrial',
+        description: `The organization switches to the free plan right away.`,
+        requestFormat: 'json',
+        parameters: [
+            {
+                name: 'organization',
+                type: 'Path',
+                schema: z.string(),
+            },
+        ],
+        response: z.void(),
+        errors: [
+            {
+                status: 400,
+                description: `API exception`,
+                schema: z
+                    .object({ error: z.boolean(), key: z.string(), message: z.string() })
+                    .passthrough(),
+            },
+            {
+                status: 401,
+                description: `Unauthenticated`,
+                schema: z.object({ message: z.string() }).passthrough(),
+            },
+            {
+                status: 403,
+                description: `Authorization error`,
+                schema: z.object({ message: z.string() }).passthrough(),
+            },
+            {
+                status: 404,
+                description: `Not found`,
+                schema: z.object({ message: z.string() }).passthrough(),
+            },
+        ],
+    },
     {
         method: 'get',
         path: '/v1/public/reports',
diff --git a/resources/js/Components/Common/UpgradeBadge.vue b/resources/js/packages/ui/src/UpgradeBadge.vue
similarity index 62%
rename from resources/js/Components/Common/UpgradeBadge.vue
rename to resources/js/packages/ui/src/UpgradeBadge.vue
index e624caec..b0196d52 100644
--- a/resources/js/Components/Common/UpgradeBadge.vue
+++ b/resources/js/packages/ui/src/UpgradeBadge.vue
@@ -1,17 +1,21 @@
 <script setup lang="ts">
 import { LockClosedIcon } from '@heroicons/vue/20/solid';
-import UpgradeModal from '@/Components/Common/UpgradeModal.vue';
+import UpgradeModal from './UpgradeModal.vue';
+import type { UpgradeFeature } from './UpgradeModal/useUpgradeCta';
 import { ref } from 'vue';
+
+defineProps<{
+    // The Professional feature behind the badge, picks the variant of the upgrade modal
+    feature: UpgradeFeature;
+}>();
+
 const showUpgradeModal = ref(false);
 </script>
 
 <template>
-    <UpgradeModal v-model:show="showUpgradeModal">
-        <slot>
-            <strong>Project and Task Estimates</strong> is only available in solidtime Professional.
-        </slot>
-    </UpgradeModal>
+    <UpgradeModal v-model:show="showUpgradeModal" :feature="feature" />
     <button
+        data-testid="upgrade_badge"
         class="inline-flex bg-secondary hover:bg-tertiary px-2 py-1 rounded border border-border-secondary hover:border-border-tertiary items-center space-x-1"
         @click.prevent="showUpgradeModal = true">
         <LockClosedIcon class="w-3 text-text-tertiary"></LockClosedIcon>
diff --git a/resources/js/packages/ui/src/UpgradeModal.vue b/resources/js/packages/ui/src/UpgradeModal.vue
new file mode 100644
index 00000000..e948aed0
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal.vue
@@ -0,0 +1,139 @@
+<script setup lang="ts">
+import { Dialog, DialogContent, DialogTitle, DialogDescription } from './dialog';
+import { LockClosedIcon } from '@heroicons/vue/16/solid';
+import { computed, type Component } from 'vue';
+import MockupBillableRates from './UpgradeModal/MockupBillableRates.vue';
+import MockupEstimates from './UpgradeModal/MockupEstimates.vue';
+import MockupGoals from './UpgradeModal/MockupGoals.vue';
+import MockupInvoicing from './UpgradeModal/MockupInvoicing.vue';
+import MockupPdfReports from './UpgradeModal/MockupPdfReports.vue';
+import MockupShareableReports from './UpgradeModal/MockupShareableReports.vue';
+import UpgradeCtaFooter from './UpgradeModal/UpgradeCtaFooter.vue';
+import { featureIcons } from './UpgradeModal/featureIcons';
+import {
+    professionalFeatures,
+    type ProfessionalFeatureKey,
+    type UpgradeFeature,
+} from './UpgradeModal/useUpgradeCta';
+
+const show = defineModel<boolean>('show', { default: false });
+
+const props = defineProps<{
+    // The Professional feature the user tried to use, picks the mock-up and the copy
+    feature: UpgradeFeature;
+}>();
+
+const contents: Record<
+    UpgradeFeature,
+    {
+        mockup: Component;
+        pill: string;
+        headline: string;
+        body: string;
+        // Feature of the pricing page that is listed first, if the feature is listed there
+        featureKey?: ProfessionalFeatureKey;
+    }
+> = {
+    'billable-rates': {
+        mockup: MockupBillableRates,
+        pill: 'Unlock billable rates',
+        headline: 'Turn tracked hours into revenue',
+        body: 'Upgrade to solidtime Professional to track billable hours',
+        featureKey: 'rates',
+    },
+    estimates: {
+        mockup: MockupEstimates,
+        pill: 'Unlock time estimates',
+        headline: 'Keep every project on budget',
+        body: 'Upgrade to solidtime Professional to set time estimates',
+        featureKey: 'estimates',
+    },
+    goals: {
+        mockup: MockupGoals,
+        pill: 'Unlock unlimited goals',
+        headline: 'Set a goal for everything that matters',
+        body: 'Upgrade to solidtime Professional to track unlimited goals',
+    },
+    invoicing: {
+        mockup: MockupInvoicing,
+        pill: 'Unlock invoicing',
+        headline: 'Get paid for every tracked hour',
+        body: 'Upgrade to solidtime Professional to create invoices',
+        featureKey: 'invoicing',
+    },
+    'pdf-reports': {
+        mockup: MockupPdfReports,
+        pill: 'Unlock PDF reports',
+        headline: 'Send reports your clients will read',
+        body: 'Upgrade to solidtime Professional to export PDF reports',
+        featureKey: 'pdf',
+    },
+    'shareable-reports': {
+        mockup: MockupShareableReports,
+        pill: 'Unlock shareable reports',
+        headline: 'Share live reports with one link',
+        body: 'Upgrade to solidtime Professional to share reports',
+        featureKey: 'shared',
+    },
+};
+
+const content = computed(() => contents[props.feature]);
+
+// The feature the user tried to use comes first
+const orderedFeatures = computed(() => [
+    ...professionalFeatures.filter((feature) => feature.key === content.value.featureKey),
+    ...professionalFeatures.filter((feature) => feature.key !== content.value.featureKey),
+]);
+</script>
+
+<template>
+    <Dialog v-model:open="show">
+        <DialogContent class="sm:max-w-xl p-0 overflow-hidden">
+            <div class="relative">
+                <component :is="content.mockup" />
+                <div
+                    class="absolute bottom-0 left-1/2 z-10 -translate-x-1/2 translate-y-1/2 whitespace-nowrap">
+                    <div
+                        class="flex items-center gap-1.5 rounded-full border border-gray-200 bg-white px-3 py-1 dark:border-border-secondary dark:bg-default-background text-xs font-medium text-text-primary shadow-sm">
+                        <LockClosedIcon class="h-3.5 w-3.5 text-accent-500 dark:text-accent-300" />
+                        {{ content.pill }}
+                    </div>
+                </div>
+            </div>
+
+            <div class="px-8 pt-9 text-center">
+                <DialogTitle class="text-xl font-semibold tracking-tight text-text-primary">
+                    {{ content.headline }}
+                </DialogTitle>
+                <DialogDescription class="mt-1.5 text-sm text-text-secondary">
+                    {{ content.body }}
+                </DialogDescription>
+            </div>
+
+            <div class="grid grid-cols-2 gap-x-6 gap-y-4 px-8 pt-9">
+                <div v-for="item in orderedFeatures" :key="item.key" class="flex gap-3">
+                    <div
+                        class="flex h-7 w-7 shrink-0 items-center justify-center rounded-md border border-border-tertiary bg-card-background">
+                        <component
+                            :is="featureIcons[item.key]"
+                            class="h-3.5 w-3.5 text-text-secondary" />
+                    </div>
+                    <div class="min-w-0">
+                        <p class="text-sm font-medium text-text-primary">{{ item.title }}</p>
+                        <p class="mt-0.5 text-xs leading-relaxed text-text-tertiary">
+                            {{ item.description }}
+                        </p>
+                    </div>
+                </div>
+            </div>
+
+            <div class="px-8 pt-9 pb-6">
+                <UpgradeCtaFooter
+                    align="stack"
+                    label="Upgrade to Professional"
+                    class="mx-auto max-w-xs"
+                    @close="show = false" />
+            </div>
+        </DialogContent>
+    </Dialog>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupBillableRates.vue b/resources/js/packages/ui/src/UpgradeModal/MockupBillableRates.vue
new file mode 100644
index 00000000..3712eede
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupBillableRates.vue
@@ -0,0 +1,39 @@
+<script setup lang="ts">
+import { LockClosedIcon } from '@heroicons/vue/16/solid';
+import MockupFrame from './MockupFrame.vue';
+
+const previewRows = [
+    { name: 'Acme Corp', duration: '42h 30min', cost: '€ 5,100.00' },
+    { name: 'Globex', duration: '27h 15min', cost: '€ 3,270.00' },
+    { name: 'Initech', duration: '12h 45min', cost: '€ 1,530.00' },
+];
+</script>
+
+<template>
+    <MockupFrame :glow-in-light-mode="false">
+        <div class="px-6 pt-4">
+            <div
+                class="grid grid-cols-[1fr_100px_100px] border-b border-gray-300/70 pb-1.5 text-[11px] text-gray-400 dark:border-white/10 dark:text-white/40">
+                <span>Client</span>
+                <span class="text-right">Duration</span>
+                <span class="flex items-center justify-end gap-1">
+                    <LockClosedIcon class="h-3 w-3" />
+                    Cost
+                </span>
+            </div>
+            <div
+                v-for="row in previewRows"
+                :key="row.name"
+                class="grid grid-cols-[1fr_100px_100px] border-b border-gray-300/50 py-1.5 text-sm last:border-b-0 dark:border-white/5">
+                <span class="text-gray-800 dark:text-white/90">{{ row.name }}</span>
+                <span class="text-right tabular-nums text-gray-500 dark:text-white/50">{{
+                    row.duration
+                }}</span>
+                <span
+                    class="select-none text-right font-medium text-accent-600 blur-[5px] dark:text-accent-300"
+                    >{{ row.cost }}</span
+                >
+            </div>
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupEstimates.vue b/resources/js/packages/ui/src/UpgradeModal/MockupEstimates.vue
new file mode 100644
index 00000000..99d12613
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupEstimates.vue
@@ -0,0 +1,48 @@
+<script setup lang="ts">
+import { LockClosedIcon } from '@heroicons/vue/16/solid';
+import MockupFrame from './MockupFrame.vue';
+
+const previewRows = [
+    { name: 'Website Redesign', spent: '32h', estimate: '40h', progress: 80, muted: false },
+    { name: 'Mobile App', spent: '11h', estimate: '20h', progress: 55, muted: true },
+    { name: 'Support Retainer', spent: '6h', estimate: '20h', progress: 30, muted: false },
+];
+</script>
+
+<template>
+    <MockupFrame :glow-in-light-mode="false">
+        <div class="px-6 pt-4">
+            <div
+                class="grid grid-cols-[1fr_170px] border-b border-gray-300/70 pb-1.5 text-[11px] text-gray-400 dark:border-white/10 dark:text-white/40">
+                <span>Project</span>
+                <span class="flex items-center gap-1">
+                    <LockClosedIcon class="h-3 w-3" />
+                    Progress
+                </span>
+            </div>
+            <div
+                v-for="row in previewRows"
+                :key="row.name"
+                class="grid grid-cols-[1fr_170px] items-center border-b border-gray-300/50 py-1.5 text-sm last:border-b-0 dark:border-white/5">
+                <span class="text-gray-800 dark:text-white/90">{{ row.name }}</span>
+                <div class="flex select-none items-center gap-2.5 blur-[3px]">
+                    <div
+                        class="h-1.5 flex-1 overflow-hidden rounded-full bg-gray-300/60 dark:bg-white/10">
+                        <div
+                            class="h-full rounded-full"
+                            :class="
+                                row.muted
+                                    ? 'bg-gray-400 dark:bg-white/40'
+                                    : 'bg-accent-500 dark:bg-accent-300'
+                            "
+                            :style="{ width: row.progress + '%' }" />
+                    </div>
+                    <span
+                        class="w-16 text-right text-xs tabular-nums text-gray-500 dark:text-white/60"
+                        >{{ row.spent }} / {{ row.estimate }}</span
+                    >
+                </div>
+            </div>
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupFrame.vue b/resources/js/packages/ui/src/UpgradeModal/MockupFrame.vue
new file mode 100644
index 00000000..694ff126
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupFrame.vue
@@ -0,0 +1,23 @@
+<script setup lang="ts">
+withDefaults(
+    defineProps<{
+        // Show the blue glow in light mode too, dark mode always has it
+        glowInLightMode?: boolean;
+    }>(),
+    { glowInLightMode: true }
+);
+</script>
+
+<template>
+    <!-- Note: Shared header of the upgrade modal, all mock-ups have the same height -->
+    <div
+        class="relative h-[156px] overflow-hidden border-b border-border-tertiary bg-background dark:border-white/10 dark:bg-[#0b1220]">
+        <!-- Note: Glow rises from behind the divider, around the pill -->
+        <div
+            :class="glowInLightMode ? '' : 'hidden dark:block'"
+            class="pointer-events-none absolute -bottom-32 left-1/2 h-56 w-[30rem] -translate-x-1/2 rounded-full bg-accent-400/25 blur-3xl dark:bg-accent-500/[0.18]" />
+        <div class="relative h-full" aria-hidden="true">
+            <slot />
+        </div>
+    </div>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupGoals.vue b/resources/js/packages/ui/src/UpgradeModal/MockupGoals.vue
new file mode 100644
index 00000000..04e685aa
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupGoals.vue
@@ -0,0 +1,54 @@
+<script setup lang="ts">
+import { LockClosedIcon } from '@heroicons/vue/16/solid';
+import MockupFrame from './MockupFrame.vue';
+
+// Note: The first goal is the one of the free plan, the others are locked
+const previewGoals = [
+    {
+        name: 'Billable hours per month',
+        tracked: '62h',
+        target: '80h',
+        progress: 78,
+        locked: false,
+    },
+    { name: 'Deep work per week', tracked: '14h', target: '20h', progress: 70, locked: true },
+    { name: 'Support per week', tracked: '3h', target: '8h', progress: 40, locked: true },
+];
+</script>
+
+<template>
+    <MockupFrame :glow-in-light-mode="false">
+        <div class="px-6 pt-4">
+            <div
+                class="grid grid-cols-[1fr_170px] border-b border-gray-300/70 pb-1.5 text-[11px] text-gray-400 dark:border-white/10 dark:text-white/40">
+                <span>Goal</span>
+                <span>Progress</span>
+            </div>
+            <div
+                v-for="goal in previewGoals"
+                :key="goal.name"
+                class="grid grid-cols-[1fr_170px] items-center border-b border-gray-300/50 py-1.5 text-sm last:border-b-0 dark:border-white/5">
+                <span class="flex items-center gap-1.5 text-gray-800 dark:text-white/90">
+                    <LockClosedIcon
+                        v-if="goal.locked"
+                        class="h-3 w-3 text-gray-400 dark:text-white/40" />
+                    {{ goal.name }}
+                </span>
+                <div
+                    class="flex select-none items-center gap-2.5"
+                    :class="goal.locked ? 'blur-[3px]' : ''">
+                    <div
+                        class="h-1.5 flex-1 overflow-hidden rounded-full bg-gray-300/60 dark:bg-white/10">
+                        <div
+                            class="h-full rounded-full bg-accent-500 dark:bg-accent-300"
+                            :style="{ width: goal.progress + '%' }" />
+                    </div>
+                    <span
+                        class="w-16 text-right text-xs tabular-nums text-gray-500 dark:text-white/60"
+                        >{{ goal.tracked }} / {{ goal.target }}</span
+                    >
+                </div>
+            </div>
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupInvoicing.vue b/resources/js/packages/ui/src/UpgradeModal/MockupInvoicing.vue
new file mode 100644
index 00000000..870933c8
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupInvoicing.vue
@@ -0,0 +1,38 @@
+<script setup lang="ts">
+import MockupFrame from './MockupFrame.vue';
+
+const lineItems = [
+    { name: 'Website Redesign', hours: '32h', amount: '€ 3,840.00' },
+    { name: 'Mobile App', hours: '18h', amount: '€ 2,160.00' },
+];
+</script>
+
+<template>
+    <MockupFrame>
+        <!-- Note: An invoice created from tracked time, it runs off the bottom edge of the header -->
+        <div
+            class="absolute left-1/2 top-5 w-60 -translate-x-1/2 rounded-t-md border border-b-0 border-gray-200 bg-white px-5 pt-4 pb-10 shadow-xl shadow-gray-400/25 dark:border-transparent dark:shadow-2xl dark:shadow-black/50">
+            <div class="flex items-start justify-between">
+                <div>
+                    <p class="text-[11px] font-semibold text-gray-900">Invoice 2026-014</p>
+                    <p class="text-[9px] text-gray-500">Acme Corp · Due November 14</p>
+                </div>
+                <span
+                    class="rounded bg-accent-500 px-1.5 py-0.5 text-[8px] font-bold tracking-wide text-white"
+                    >SENT</span
+                >
+            </div>
+            <div class="mt-3 space-y-1 text-[9px] text-gray-600">
+                <div v-for="item in lineItems" :key="item.name" class="flex justify-between">
+                    <span>{{ item.name }} · {{ item.hours }}</span>
+                    <span class="tabular-nums">{{ item.amount }}</span>
+                </div>
+            </div>
+            <div
+                class="mt-2 flex justify-between border-t border-gray-200 pt-1.5 text-[10px] font-semibold text-gray-900">
+                <span>Total</span>
+                <span class="tabular-nums">€ 6,000.00</span>
+            </div>
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupPdfPage.vue b/resources/js/packages/ui/src/UpgradeModal/MockupPdfPage.vue
new file mode 100644
index 00000000..80fb39e9
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupPdfPage.vue
@@ -0,0 +1,35 @@
+<script setup lang="ts">
+const bars = [45, 70, 55, 85, 65, 35, 50];
+</script>
+
+<template>
+    <!-- Note: A PDF page that runs off the bottom edge of the header -->
+    <div
+        class="rounded-t-md border border-b-0 border-gray-200 bg-white px-5 pt-4 pb-10 shadow-xl shadow-gray-400/25 dark:border-transparent dark:shadow-2xl dark:shadow-black/50">
+        <div class="flex items-start justify-between">
+            <div>
+                <p class="text-[11px] font-semibold text-gray-900">Time report</p>
+                <p class="text-[9px] text-gray-500">Acme Corp · October 2026</p>
+            </div>
+            <span
+                class="rounded bg-red-500 px-1.5 py-0.5 text-[8px] font-bold tracking-wide text-white"
+                >PDF</span
+            >
+        </div>
+        <div class="mt-2.5 flex h-7 items-end gap-1">
+            <div
+                v-for="(height, index) in bars"
+                :key="index"
+                class="flex-1 rounded-sm bg-accent-500/70"
+                :style="{ height: height + '%' }" />
+        </div>
+        <div class="mt-2 space-y-1 text-[9px] text-gray-600">
+            <div class="flex justify-between">
+                <span>Website Redesign</span><span class="tabular-nums">32h 15min</span>
+            </div>
+            <div class="flex justify-between">
+                <span>Mobile App</span><span class="tabular-nums">18h 40min</span>
+            </div>
+        </div>
+    </div>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupPdfReports.vue b/resources/js/packages/ui/src/UpgradeModal/MockupPdfReports.vue
new file mode 100644
index 00000000..7ccbb6cf
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupPdfReports.vue
@@ -0,0 +1,17 @@
+<script setup lang="ts">
+import MockupFrame from './MockupFrame.vue';
+import MockupPdfPage from './MockupPdfPage.vue';
+</script>
+
+<template>
+    <MockupFrame>
+        <!-- Note: The PDF report with two more pages fanned out behind it -->
+        <div class="absolute left-1/2 top-5 h-full w-56 -translate-x-1/2">
+            <div
+                class="absolute inset-x-0 top-3 h-48 origin-bottom -translate-x-10 -rotate-[8deg] rounded-md border border-gray-200 bg-white/80 shadow-lg shadow-gray-400/20 dark:border-transparent dark:bg-white/70 dark:shadow-xl dark:shadow-black/40" />
+            <div
+                class="absolute inset-x-0 top-3 h-48 origin-bottom translate-x-10 rotate-[8deg] rounded-md border border-gray-200 bg-white/80 shadow-lg shadow-gray-400/20 dark:border-transparent dark:bg-white/70 dark:shadow-xl dark:shadow-black/40" />
+            <MockupPdfPage class="absolute inset-x-0 top-0" />
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/MockupShareableReports.vue b/resources/js/packages/ui/src/UpgradeModal/MockupShareableReports.vue
new file mode 100644
index 00000000..0ca65244
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/MockupShareableReports.vue
@@ -0,0 +1,50 @@
+<script setup lang="ts">
+import { LinkIcon, LockClosedIcon } from '@heroicons/vue/16/solid';
+import MockupFrame from './MockupFrame.vue';
+
+const previewRows = [
+    { name: 'Website Redesign', duration: '32h 15min' },
+    { name: 'Mobile App', duration: '18h 40min' },
+];
+</script>
+
+<template>
+    <MockupFrame>
+        <!-- Note: A browser window showing the shared report, it runs into the bottom edge -->
+        <div
+            class="absolute inset-x-10 top-4 -bottom-px rounded-t-lg border border-b-0 border-gray-300/80 bg-white shadow-xl shadow-gray-400/20 dark:border-white/10 dark:bg-white/[0.04] dark:shadow-2xl dark:shadow-black/40">
+            <div
+                class="flex items-center gap-2 border-b border-gray-200 px-3 py-2 dark:border-white/10">
+                <div class="flex gap-1">
+                    <span class="h-2 w-2 rounded-full bg-gray-300 dark:bg-white/15" />
+                    <span class="h-2 w-2 rounded-full bg-gray-300 dark:bg-white/15" />
+                    <span class="h-2 w-2 rounded-full bg-gray-300 dark:bg-white/15" />
+                </div>
+                <div
+                    class="flex min-w-0 flex-1 items-center gap-1.5 rounded-md bg-gray-100 px-2 py-1 text-[11px] text-gray-500 dark:bg-black/30 dark:text-white/50">
+                    <LockClosedIcon class="h-3 w-3 shrink-0 text-gray-400 dark:text-white/30" />
+                    <span class="truncate">app.solidtime.io/shared-report</span>
+                </div>
+                <span
+                    class="flex shrink-0 items-center gap-1 rounded-md border border-gray-200 bg-gray-50 px-2 py-1 text-[11px] font-medium text-gray-700 dark:border-transparent dark:bg-white/15 dark:text-white/90">
+                    <LinkIcon class="h-3 w-3" />
+                    Copy link
+                </span>
+            </div>
+            <div class="px-4 pt-2 pb-1.5">
+                <p class="py-1.5 text-xs font-medium text-gray-900 dark:text-white/90">
+                    Acme Corp · October
+                </p>
+                <div
+                    v-for="row in previewRows"
+                    :key="row.name"
+                    class="flex justify-between border-b border-gray-100 py-1 text-xs last:border-b-0 dark:border-white/5">
+                    <span class="text-gray-600 dark:text-white/70">{{ row.name }}</span>
+                    <span class="tabular-nums text-gray-400 dark:text-white/50">{{
+                        row.duration
+                    }}</span>
+                </div>
+            </div>
+        </div>
+    </MockupFrame>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/UpgradeCtaFooter.vue b/resources/js/packages/ui/src/UpgradeModal/UpgradeCtaFooter.vue
new file mode 100644
index 00000000..0398fd44
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/UpgradeCtaFooter.vue
@@ -0,0 +1,78 @@
+<script setup lang="ts">
+import { ArrowTopRightOnSquareIcon } from '@heroicons/vue/16/solid';
+import { pricingUrl, useUpgradeCta } from './useUpgradeCta';
+
+const props = withDefaults(
+    defineProps<{
+        label?: string;
+        align?: 'between' | 'end' | 'stack';
+        showCompare?: boolean;
+    }>(),
+    { label: 'Upgrade to Professional', align: 'between', showCompare: true }
+);
+
+const emit = defineEmits<{ close: [] }>();
+const { canUpgrade, goToBilling } = useUpgradeCta();
+</script>
+
+<template>
+    <div
+        :class="
+            props.align === 'stack'
+                ? 'flex flex-col items-center gap-3'
+                : 'flex flex-wrap items-center gap-2'
+        ">
+        <a
+            v-if="props.align !== 'stack' && props.showCompare"
+            :href="pricingUrl"
+            target="_blank"
+            rel="noopener"
+            class="mr-auto inline-flex items-center gap-1 text-xs text-text-tertiary transition-colors hover:text-text-primary">
+            Compare plans
+            <ArrowTopRightOnSquareIcon class="h-3 w-3" />
+        </a>
+        <template v-if="canUpgrade">
+            <button
+                v-if="props.align !== 'stack'"
+                type="button"
+                class="h-9 whitespace-nowrap rounded-md px-3 text-sm font-medium text-text-secondary transition-colors hover:bg-white/5 hover:text-text-primary"
+                @click="emit('close')">
+                Not now
+            </button>
+            <button
+                type="button"
+                data-testid="upgrade_modal_cta"
+                class="h-9 whitespace-nowrap rounded-md bg-accent-500 px-4 text-sm font-semibold text-white shadow-[0_0_24px_-6px] shadow-accent-500/60 transition-colors hover:bg-accent-400 focus:outline-none focus-visible:ring-2 focus-visible:ring-ring"
+                :class="props.align === 'stack' ? 'w-full' : ''"
+                @click="goToBilling">
+                {{ props.label }}
+            </button>
+        </template>
+        <template v-else>
+            <span class="text-xs text-text-tertiary">Only the organization owner can upgrade.</span>
+            <button
+                type="button"
+                class="h-9 rounded-md border border-border-secondary px-3 text-sm font-medium text-text-primary transition-colors hover:bg-white/5"
+                @click="emit('close')">
+                Got it
+            </button>
+        </template>
+        <div v-if="props.align === 'stack'" class="flex items-center gap-4 text-xs">
+            <button
+                v-if="canUpgrade"
+                type="button"
+                class="text-text-tertiary transition-colors hover:text-text-primary"
+                @click="emit('close')">
+                Not now
+            </button>
+            <a
+                :href="pricingUrl"
+                target="_blank"
+                rel="noopener"
+                class="inline-flex items-center gap-1 text-text-tertiary transition-colors hover:text-text-primary">
+                Compare plans
+                <ArrowTopRightOnSquareIcon class="h-3 w-3" />
+            </a>
+        </div>
+    </div>
+</template>
diff --git a/resources/js/packages/ui/src/UpgradeModal/featureIcons.ts b/resources/js/packages/ui/src/UpgradeModal/featureIcons.ts
new file mode 100644
index 00000000..a38a10e1
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/featureIcons.ts
@@ -0,0 +1,19 @@
+import type { Component } from 'vue';
+import {
+    AdjustmentsHorizontalIcon,
+    ClockIcon,
+    CurrencyEuroIcon,
+    DocumentArrowDownIcon,
+    DocumentTextIcon,
+    LinkIcon,
+} from '@heroicons/vue/16/solid';
+import type { ProfessionalFeatureKey } from './useUpgradeCta';
+
+export const featureIcons: Record<ProfessionalFeatureKey, Component> = {
+    rates: CurrencyEuroIcon,
+    invoicing: DocumentTextIcon,
+    estimates: ClockIcon,
+    rounding: AdjustmentsHorizontalIcon,
+    pdf: DocumentArrowDownIcon,
+    shared: LinkIcon,
+};
diff --git a/resources/js/packages/ui/src/UpgradeModal/useUpgradeCta.ts b/resources/js/packages/ui/src/UpgradeModal/useUpgradeCta.ts
new file mode 100644
index 00000000..01f0368d
--- /dev/null
+++ b/resources/js/packages/ui/src/UpgradeModal/useUpgradeCta.ts
@@ -0,0 +1,72 @@
+import { computed, inject, type ComputedRef, type InjectionKey } from 'vue';
+
+export interface UpgradeCta {
+    canUpgrade: ComputedRef<boolean>;
+    goToBilling: () => void;
+}
+
+export const upgradeCtaKey: InjectionKey<UpgradeCta> = Symbol('upgradeCta');
+
+/**
+ * Shared call to action for the upgrade modal variations: members who can manage billing are
+ * sent to the billing page, everyone else is asked to contact the organization owner.
+ *
+ * The app layout provides who can upgrade and how to get to the billing page. Without a
+ * provider (e.g. other consumers of this package) nobody can upgrade from the modal.
+ */
+export function useUpgradeCta(): UpgradeCta {
+    return inject(upgradeCtaKey, {
+        canUpgrade: computed(() => false),
+        goToBilling: () => {},
+    });
+}
+
+// Note: Copy mirrors https://www.solidtime.io/pricing so the gate and the pricing page match.
+export const pricingUrl = 'https://www.solidtime.io/pricing';
+
+// Professional features the upgrade modal has a variant for
+export type UpgradeFeature =
+    'billable-rates' | 'estimates' | 'goals' | 'invoicing' | 'pdf-reports' | 'shareable-reports';
+
+export type ProfessionalFeatureKey =
+    'rates' | 'invoicing' | 'estimates' | 'rounding' | 'pdf' | 'shared';
+
+export type ProfessionalFeature = {
+    key: ProfessionalFeatureKey;
+    title: string;
+    description: string;
+};
+
+// Note: Billing and reporting features of the Professional plan on https://www.solidtime.io/pricing
+export const professionalFeatures: ProfessionalFeature[] = [
+    {
+        key: 'rates',
+        title: 'Billable rates',
+        description: 'Set rates per organization, project or member.',
+    },
+    {
+        key: 'invoicing',
+        title: 'Invoicing',
+        description: 'Create invoices straight from your tracked time.',
+    },
+    {
+        key: 'estimates',
+        title: 'Time estimates',
+        description: 'Budget hours per project and task and see what is left.',
+    },
+    {
+        key: 'rounding',
+        title: 'Rounding',
+        description: 'Round time in reports, e.g. to 15 minutes.',
+    },
+    {
+        key: 'pdf',
+        title: 'PDF reports',
+        description: 'Export clean reports to send to clients.',
+    },
+    {
+        key: 'shared',
+        title: 'Shareable reports',
+        description: 'Share a live report link, no login needed.',
+    },
+];
diff --git a/resources/js/packages/ui/src/index.ts b/resources/js/packages/ui/src/index.ts
index 68e928e8..72673f40 100644
--- a/resources/js/packages/ui/src/index.ts
+++ b/resources/js/packages/ui/src/index.ts
@@ -21,6 +21,8 @@ export type { CalendarSettings } from './FullCalendar/calendarSettings';
 export type { ActivityPeriod } from './FullCalendar/activityTypes';
 export { cn } from './utils/cn';
 export { useCssVariable } from './utils/useCssVariable';
+export { upgradeCtaKey, useUpgradeCta } from './UpgradeModal/useUpgradeCta';
+export type { UpgradeCta, UpgradeFeature } from './UpgradeModal/useUpgradeCta';
 
 import Badge from './Badge.vue';
 import Button from './Buttons/Button.vue';
@@ -162,6 +164,8 @@ import { Tabs, TabsContent, TabsList, TabsTrigger } from './tabs/index';
 import TabBar from './TabBar/TabBar.vue';
 import TabBarItem from './TabBar/TabBarItem.vue';
 import TimezoneMismatchModal from './TimezoneMismatchModal.vue';
+import UpgradeBadge from './UpgradeBadge.vue';
+import UpgradeModal from './UpgradeModal.vue';
 import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from './tooltip/index';
 
 export {
@@ -305,4 +309,6 @@ export {
     TooltipContent,
     TooltipProvider,
     TooltipTrigger,
+    UpgradeBadge,
+    UpgradeModal,
 };