Add checks for placeholder invitation; Fixed bug in member deletion

app/Console/Kernel.php

@@ -28,7 +28,7 @@ class Kernel extends ConsoleKernel
 
         $schedule->command('self-host:database-consistency')
             ->when(fn (): bool => config('scheduling.tasks.self_hosting_database_consistency'))
-            ->twiceDaily();
+            ->everySixHours();
     }
 
     /**

app/Exceptions/Api/InvitationForTheEmailAlreadyExistsApiException.php

@@ -0,0 +1,10 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Exceptions\Api;
+
+class InvitationForTheEmailAlreadyExistsApiException extends ApiException
+{
+    public const string KEY = 'invitation_for_the_email_already_exists';
+}

app/Http/Controllers/Api/V1/InvitationController.php

@@ -4,6 +4,7 @@ declare(strict_types=1);
 
 namespace App\Http\Controllers\Api\V1;
 
+use App\Exceptions\Api\InvitationForTheEmailAlreadyExistsApiException;
 use App\Exceptions\Api\UserIsAlreadyMemberOfOrganizationApiException;
 use App\Http\Requests\V1\Invitation\InvitationIndexRequest;
 use App\Http\Requests\V1\Invitation\InvitationStoreRequest;
@@ -50,6 +51,7 @@ class InvitationController extends Controller
      *
      * @throws AuthorizationException
      * @throws UserIsAlreadyMemberOfOrganizationApiException
+     * @throws InvitationForTheEmailAlreadyExistsApiException
      *
      * @operationId invite
      */

app/Http/Controllers/Api/V1/MemberController.php

@@ -10,6 +10,7 @@ use App\Exceptions\Api\CanNotRemoveOwnerFromOrganization;
 use App\Exceptions\Api\ChangingRoleOfPlaceholderIsNotAllowed;
 use App\Exceptions\Api\ChangingRoleToPlaceholderIsNotAllowed;
 use App\Exceptions\Api\EntityStillInUseApiException;
+use App\Exceptions\Api\InvitationForTheEmailAlreadyExistsApiException;
 use App\Exceptions\Api\OnlyOwnerCanChangeOwnership;
 use App\Exceptions\Api\OnlyPlaceholdersCanBeMergedIntoAnotherMember;
 use App\Exceptions\Api\OrganizationNeedsAtLeastOneOwner;
@@ -173,6 +174,7 @@ class MemberController extends Controller
      * @throws UserNotPlaceholderApiException
      * @throws UserIsAlreadyMemberOfOrganizationApiException
      * @throws ThisPlaceholderCanNotBeInvitedUseTheMergeToolInsteadException
+     * @throws InvitationForTheEmailAlreadyExistsApiException
      *
      * @operationId invitePlaceholder
      */

app/Http/Controllers/Controller.php

@@ -43,7 +43,10 @@ class Controller extends BaseController
         /** @var Member|null $member */
         $member = Member::query()->whereBelongsTo($organization, 'organization')->whereBelongsTo($user, 'user')->first();
         if ($member === null) {
-            Log::error('This function should only be called in authenticated context after checking the user is a member of the organization');
+            Log::error('This function should only be called in authenticated context after checking the user is a member of the organization', [
+                'user' => $user->getKey(),
+                'organization' => $organization->getKey(),
+            ]);
             throw new AuthorizationException;
         }
 

app/Http/Requests/V1/Invitation/InvitationStoreRequest.php

@@ -7,11 +7,8 @@ namespace App\Http\Requests\V1\Invitation;
 use App\Enums\Role;
 use App\Http\Requests\V1\BaseFormRequest;
 use App\Models\Organization;
-use App\Models\OrganizationInvitation;
 use Illuminate\Contracts\Validation\ValidationRule;
-use Illuminate\Database\Eloquent\Builder;
 use Illuminate\Validation\Rule;
-use Korridor\LaravelModelValidationRules\Rules\UniqueEloquent;
 
 /**
  * @property Organization $organization
@@ -29,10 +26,6 @@ class InvitationStoreRequest extends BaseFormRequest
             'email' => [
                 'required',
                 'email',
-                UniqueEloquent::make(OrganizationInvitation::class, 'email', function (Builder $builder): Builder {
-                    /** @var Builder<OrganizationInvitation> $builder */
-                    return $builder->whereBelongsTo($this->organization, 'organization');
-                })->withCustomTranslation('validation.invitation_already_exists'),
             ],
             'role' => [
                 'required',

app/Service/InvitationService.php

@@ -5,6 +5,7 @@ declare(strict_types=1);
 namespace App\Service;
 
 use App\Enums\Role;
+use App\Exceptions\Api\InvitationForTheEmailAlreadyExistsApiException;
 use App\Exceptions\Api\UserIsAlreadyMemberOfOrganizationApiException;
 use App\Mail\OrganizationInvitationMail;
 use App\Models\Member;
@@ -16,7 +17,7 @@ use Laravel\Jetstream\Events\InvitingTeamMember;
 class InvitationService
 {
     /**
-     * @throws UserIsAlreadyMemberOfOrganizationApiException
+     * @throws UserIsAlreadyMemberOfOrganizationApiException|InvitationForTheEmailAlreadyExistsApiException
      */
     public function inviteUser(Organization $organization, string $email, Role $role): OrganizationInvitation
     {
@@ -28,6 +29,13 @@ class InvitationService
             throw new UserIsAlreadyMemberOfOrganizationApiException;
         }
 
+        if (OrganizationInvitation::query()
+            ->where('email', $email)
+            ->whereBelongsTo($organization, 'organization')
+            ->exists()) {
+            throw new InvitationForTheEmailAlreadyExistsApiException;
+        }
+
         InvitingTeamMember::dispatch($organization, $email, $role->value);
 
         $invitation = new OrganizationInvitation;

app/Service/MemberService.php

@@ -67,6 +67,14 @@ class MemberService
             throw new CanNotRemoveOwnerFromOrganization;
         }
 
+        $user = $member->user;
+        $isPlaceholder = $user->is_placeholder;
+
+        if (! $isPlaceholder && $user->current_team_id === $member->organization_id) {
+            $user->currentTeam()->disassociate();
+            $user->save();
+        }
+
         if ($withRelations) {
             TimeEntry::query()->where('user_id', $member->user_id)->whereBelongsTo($organization, 'organization')->delete();
             ProjectMember::query()->whereBelongsToOrganization($organization)->where('user_id', $member->user_id)->delete();
@@ -80,6 +88,14 @@ class MemberService
         }
 
         $member->delete();
+
+        if ($isPlaceholder) {
+            $user->delete();
+        } else {
+            $this->userService->makeSureUserHasAtLeastOneOrganization($user);
+            $this->userService->makeSureUserHasCurrentOrganization($user);
+        }
+
         MemberRemoved::dispatch($member, $organization);
     }
 

lang/en/exceptions.php

@@ -9,6 +9,7 @@ use App\Exceptions\Api\ChangingRoleToPlaceholderIsNotAllowed;
 use App\Exceptions\Api\EntityStillInUseApiException;
 use App\Exceptions\Api\FeatureIsNotAvailableInFreePlanApiException;
 use App\Exceptions\Api\InactiveUserCanNotBeUsedApiException;
+use App\Exceptions\Api\InvitationForTheEmailAlreadyExistsApiException;
 use App\Exceptions\Api\OnlyOwnerCanChangeOwnership;
 use App\Exceptions\Api\OnlyPlaceholdersCanBeMergedIntoAnotherMember;
 use App\Exceptions\Api\OrganizationHasNoSubscriptionButMultipleMembersException;
@@ -45,6 +46,7 @@ return [
         ChangingRoleOfPlaceholderIsNotAllowed::KEY => 'Changing role of placeholder is not allowed',
         OnlyPlaceholdersCanBeMergedIntoAnotherMember::KEY => 'Only placeholders can be merged into another member',
         ThisPlaceholderCanNotBeInvitedUseTheMergeToolInsteadException::KEY => 'This placeholder can not be invited use the merge tool instead',
+        InvitationForTheEmailAlreadyExistsApiException::KEY => 'The email has already been invited to the organization. Please wait for the user to accept the invitation or resend the invitation email.',
     ],
     'unknown_error_in_admin_panel' => 'An unknown error occurred. Please check the logs.',
 ];

resources/js/Components/ui/calendar/CalendarDateInput.vue

@@ -6,8 +6,8 @@ import {
 } from '@/Components/ui/popover';
 import { Button } from '@/Components/ui/button';
 import { Calendar } from '@/Components/ui/calendar';
-import { CalendarIcon, XIcon } from 'lucide-vue-next';
-import { formatDate } from '@/packages/ui/src/utils/time';
+import { CalendarIcon } from 'lucide-vue-next';
+import { formatDateLocalized } from '@/packages/ui/src/utils/time';
 import { parseDate } from '@internationalized/date';
 import { computed, inject, type ComputedRef } from 'vue';
 import { type Organization } from '@/packages/api/src';
@@ -17,10 +17,6 @@ const emit = defineEmits<{
     blur: [];
 }>();
 
-defineProps<{
-    clearable?: boolean;
-}>();
-
 const handleChange = (date: string) => {
     model.value = date;
 };
@@ -29,11 +25,6 @@ const handleBlur = () => {
     emit('blur');
 };
 
-const handleClear = (event: Event) => {
-    event.stopPropagation();
-    model.value = null;
-};
-
 const date = computed(() => {
     return model.value ? parseDate(model.value) : undefined;
 });
@@ -53,17 +44,7 @@ const organization = inject<ComputedRef<Organization>>('organization');
                 ]"
             >
                 <CalendarIcon class="mr-2 h-4 w-4" />
-                <span class="flex-1">
-                    {{ model ? formatDate(model, organization?.date_format) : 'Pick a date' }}
-                </span>
-                <button
-                    v-if="clearable && model"
-                    class="ml-2 hover:bg-muted rounded p-1 transition-colors"
-                    type="button"
-                    @click="handleClear"
-                >
-                    <XIcon class="h-4 w-4" />
-                </button>
+                {{ model ? formatDateLocalized(model, organization?.date_format) : 'Pick a date' }}
             </Button>
         </PopoverTrigger>
         <PopoverContent class="w-auto p-0">

resources/js/packages/api/src/openapi.json.client.ts

@@ -67,7 +67,6 @@ const InvoiceResource = z
         status: z.string(),
         date: z.string(),
         due_at: z.string(),
-        paid_date: z.string(),
         created_at: z.union([z.string(), z.null()]),
         updated_at: z.union([z.string(), z.null()]),
     })
@@ -77,7 +76,7 @@ const InvoiceDiscountType = z.enum(['percentage', 'fixed']);
 const InvoiceStoreRequest = z
     .object({
         due_at: z.union([z.string(), z.null()]).optional(),
-        paid_date: z.union([z.string(), z.null()]).optional(),
+        paid_at: z.union([z.string(), z.null()]).optional(),
         seller_name: z.string(),
         seller_vatin: z.union([z.string(), z.null()]).optional(),
         seller_address_line_1: z.union([z.string(), z.null()]).optional(),
@@ -103,13 +102,8 @@ const InvoiceStoreRequest = z
         billing_period_end: z.union([z.string(), z.null()]).optional(),
         reference: z.string(),
         currency: z.string(),
-        tax_rate: z.number().int().gte(0).lte(2147483647).optional(),
-        discount_amount: z
-            .number()
-            .int()
-            .gte(0)
-            .lte(9223372036854776000)
-            .optional(),
+        tax_rate: z.number().int().optional(),
+        discount_amount: z.number().int().optional(),
         discount_type: InvoiceDiscountType.optional(),
         footer: z.union([z.string(), z.null()]).optional(),
         notes: z.union([z.string(), z.null()]).optional(),
@@ -121,12 +115,8 @@ const InvoiceStoreRequest = z
                     .object({
                         name: z.string(),
                         description: z.union([z.string(), z.null()]).optional(),
-                        unit_price: z
-                            .number()
-                            .int()
-                            .gte(0)
-                            .lte(9223372036854776000),
-                        quantity: z.number().gte(0).lte(99999999),
+                        unit_price: z.number().int().gte(0).lte(99999999),
+                        quantity: z.number().gte(0),
                     })
                     .passthrough()
             )
@@ -171,7 +161,7 @@ const DetailedInvoiceResource = z
         buyer_address_country: z.string(),
         buyer_phone: z.string(),
         buyer_email: z.string(),
-        paid_date: z.string(),
+        paid_at: z.union([z.string(), z.null()]),
         due_at: z.string(),
         discount_type: z.string(),
         discount_amount: z.number().int(),
@@ -195,7 +185,7 @@ const InvoiceUpdateRequest = z
     .object({
         status: InvoiceStatus,
         due_at: z.union([z.string(), z.null()]),
-        paid_date: z.union([z.string(), z.null()]),
+        paid_at: z.union([z.string(), z.null()]),
         seller_name: z.string(),
         seller_vatin: z.union([z.string(), z.null()]),
         seller_address_line_1: z.union([z.string(), z.null()]),
@@ -221,8 +211,8 @@ const InvoiceUpdateRequest = z
         billing_period_end: z.union([z.string(), z.null()]),
         reference: z.string(),
         currency: z.string(),
-        tax_rate: z.number().int().gte(0).lte(2147483647),
-        discount_amount: z.number().int().gte(0).lte(9223372036854776000),
+        tax_rate: z.number().int(),
+        discount_amount: z.number().int(),
         discount_type: InvoiceDiscountType,
         footer: z.union([z.string(), z.null()]),
         notes: z.union([z.string(), z.null()]),
@@ -234,12 +224,8 @@ const InvoiceUpdateRequest = z
                     id: z.union([z.string(), z.null()]).optional(),
                     name: z.string(),
                     description: z.union([z.string(), z.null()]).optional(),
-                    unit_price: z
-                        .number()
-                        .int()
-                        .gte(0)
-                        .lte(9223372036854776000),
-                    quantity: z.number().gte(0).lte(99999999),
+                    unit_price: z.number().int().gte(0).lte(99999999),
+                    quantity: z.number().gte(0),
                 })
                 .passthrough()
         ),

resources/js/packages/ui/src/TimeEntry/TimeEntryAggregateRow.vue

@@ -154,13 +154,13 @@ function onSelectChange(checked: boolean) {
                         "></BillableToggleButton>
                     <div class="flex-1">
                         <button
-                            :class="twMerge('text-text-secondary w-[110px] px-1 py-1.5 bg-transparent text-center hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-medium focus-visible:outline-none focus:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:bg-tertiary', organization?.time_format === '12-hours' ? 'w-[160px]' : 'w-[110px]')"
+                            :class="twMerge('hidden lg:block text-text-secondary w-[110px] px-1 py-1.5 bg-transparent text-center hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-medium focus-visible:outline-none focus:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:bg-tertiary', organization?.time_format === '12-hours' ? 'w-[160px]' : 'w-[110px]')"
                             @click="expanded = !expanded">
                             {{ formatStartEnd(timeEntry.start, timeEntry.end, organization?.time_format) }}
                         </button>
                     </div>
                     <button
-                        class="text-text-primary min-w-[90px] px-2.5 py-1.5 bg-transparent text-right hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-medium focus-visible:outline-none focus:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:bg-tertiary"
+                        class="text-text-primary min-w-[90px] px-2.5 py-1.5 bg-transparent text-right hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-semibold focus-visible:outline-none focus:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:bg-tertiary"
                         @click="expanded = !expanded">
                         {{
                             formatHumanReadableDuration(
@@ -173,7 +173,7 @@ function onSelectChange(checked: boolean) {
 
                     <TimeTrackerStartStop
                         :active="!!(timeEntry.start && !timeEntry.end)"
-                        class="opacity-20 flex group-hover:opacity-100 focus-visible:opacity-100"
+                        class="opacity-20 hidden sm:flex group-hover:opacity-100 focus-visible:opacity-100"
                         @changed="
                             onStartStopClick(timeEntry)
                         "></TimeTrackerStartStop>

resources/js/packages/ui/src/TimeEntry/TimeEntryRow.vue

@@ -144,6 +144,7 @@ function onSelectChange(checked : boolean) {
                         "></BillableToggleButton>
                     <div class="flex-1">
                         <TimeEntryRangeSelector
+                            class="hidden lg:block"
                             :start="timeEntry.start"
                             :end="timeEntry.end"
                             :show-date
@@ -159,7 +160,7 @@ function onSelectChange(checked : boolean) {
                         "></TimeEntryRowDurationInput>
                     <TimeTrackerStartStop
                         :active="!!(timeEntry.start && !timeEntry.end)"
-                        class="opacity-20 flex focus-visible:opacity-100 group-hover:opacity-100"
+                        class="opacity-20 hidden sm:flex focus-visible:opacity-100 group-hover:opacity-100"
                         @changed="onStartStopClick"></TimeTrackerStartStop>
                     <TimeEntryMoreOptionsDropdown
                         @delete="

resources/js/packages/ui/src/TimeEntry/TimeEntryRowDurationInput.vue

@@ -82,7 +82,7 @@ function selectInput(event: Event) {
         v-model="currentTime"
         data-testid="time_entry_duration_input"
         name="Duration"
-        class="text-text-primary w-[90px] px-2.5 py-1.5 bg-transparent text-right hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-medium focus-visible:bg-tertiary focus-visible:border-transparent focus-visible:ring-2 focus-visible:ring-ring"
+        class="text-text-primary w-[90px] px-2.5 py-1.5 bg-transparent text-right hover:bg-card-background rounded-lg border border-transparent hover:border-card-border text-sm font-semibold focus-visible:bg-tertiary focus-visible:border-transparent focus-visible:ring-2 focus-visible:ring-ring"
         @focus="selectInput"
         @keydown.tab="open = false"
         @blur="updateTimerAndStartLiveTimerUpdate"

resources/js/packages/ui/src/utils/time.ts

@@ -160,29 +160,12 @@ export function formatWeek(date: string | null): string {
  * @param date - date in the format of 'YYYY-MM-DD'
  */
 export function formatHumanReadableDate(date: string) {
-    const dateObj = dayjs(date);
-    const today = dayjs();
-    
-    if (dateObj.isToday()) {
+    if (dayjs(date).isToday()) {
         return 'Today';
-    } else if (dateObj.isYesterday()) {
+    } else if (dayjs(date).isYesterday()) {
         return 'Yesterday';
     }
-    
-    // Calculate difference in days
-    const diffInDays = today.diff(dateObj, 'day');
-    
-    if (diffInDays > 0 && diffInDays <= 30) {
-        // For dates in the past (2-30 days ago)
-        return `${diffInDays} ${diffInDays === 1 ? 'day' : 'days'} ago`;
-    } else if (diffInDays < 0 && diffInDays >= -30) {
-        // For dates in the future (within 30 days)
-        const futureDays = Math.abs(diffInDays);
-        return `In ${futureDays} ${futureDays === 1 ? 'day' : 'days'}`;
-    }
-    
-    // For dates older than 30 days, show the actual date
-    return dateObj.format('MMM D, YYYY');
+    return dayjs(date).fromNow();
 }
 
 export function formatWeekday(date: string) {

tests/Unit/Endpoint/Api/V1/InvitationEndpointTest.php

@@ -129,26 +129,31 @@ class InvitationEndpointTest extends ApiEndpointTestAbstract
         $response->assertJsonPath('message', 'User is already a member of the organization');
     }
 
-    public function test_store_fails_if_user_invites_user_who_is_already_invited_to_organization(): void
+    public function test_store_fails_if_an_invitation_with_the_same_email_already_exists(): void
     {
         // Arrange
         $data = $this->createUserWithPermission([
             'invitations:create',
         ]);
         Passport::actingAs($data->user);
-        $invitation = OrganizationInvitation::factory()->forOrganization($data->organization)->create();
+        $email = 'user@email.test';
+        $invitation = OrganizationInvitation::factory()->forOrganization($data->organization)->create([
+            'email' => $email,
+        ]);
 
         // Act
         $response = $this->postJson(route('api.v1.invitations.store', $data->organization->getKey()), [
-            'email' => $invitation->email,
+            'email' => $email,
             'role' => Role::Employee->value,
         ]);
 
         // Assert
-        $response->assertInvalid([
-            'email' => 'The email has already been invited to the organization. Please wait for the user to accept the invitation or resend the invitation email.',
+        $response->assertStatus(400);
+        $response->assertExactJson([
+            'error' => true,
+            'key' => 'invitation_for_the_email_already_exists',
+            'message' => 'The email has already been invited to the organization. Please wait for the user to accept the invitation or resend the invitation email.',
         ]);
-        $response->assertStatus(422);
     }
 
     public function test_store_works_if_user_invites_user_who_is_also_a_placeholder(): void

tests/Unit/Endpoint/Api/V1/MemberEndpointTest.php

@@ -10,6 +10,7 @@ use App\Events\MemberRemoved;
 use App\Http\Controllers\Api\V1\MemberController;
 use App\Models\Member;
 use App\Models\Organization;
+use App\Models\OrganizationInvitation;
 use App\Models\Project;
 use App\Models\ProjectMember;
 use App\Models\TimeEntry;
@@ -653,6 +654,103 @@ class MemberEndpointTest extends ApiEndpointTestAbstract
         Event::assertNotDispatched(MemberRemoved::class);
     }
 
+    public function test_destroy_endpoint_also_deletes_user_if_member_is_placeholder(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:delete',
+        ]);
+        $user = User::factory()->placeholder()->create();
+        $member = Member::factory()->forUser($user)->forOrganization($data->organization)->role(Role::Placeholder)->create();
+        Passport::actingAs($data->user);
+        Event::fake([
+            MemberRemoved::class,
+        ]);
+
+        // Act
+        $response = $this->deleteJson(route('api.v1.members.destroy', [$data->organization->getKey(), $member->getKey()]));
+
+        // Assert
+        $response->assertStatus(204);
+        $this->assertDatabaseMissing(Member::class, [
+            'id' => $member->getKey(),
+        ]);
+        $this->assertDatabaseMissing(User::class, [
+            'id' => $user->getKey(),
+        ]);
+        Event::assertDispatched(function (MemberRemoved $event) use ($data, $member): bool {
+            return $event->organization->is($data->organization) &&
+                $event->member->is($member);
+        }, 1);
+    }
+
+    public function test_destroy_endpoint_sets_current_organization_to_organization_the_user_is_still_member_of(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:delete',
+        ]);
+        $user = $data->user;
+        $otherOrganization = Organization::factory()->create();
+        $otherMember = Member::factory()->forOrganization($otherOrganization)->forUser($user)->role(Role::Employee)->create();
+        Passport::actingAs($user);
+        Event::fake([
+            MemberRemoved::class,
+        ]);
+
+        // Act
+        $response = $this->deleteJson(route('api.v1.members.destroy', [$data->organization->getKey(), $data->member->getKey()]));
+
+        // Assert
+        $response->assertStatus(204);
+        $this->assertDatabaseMissing(Member::class, [
+            'id' => $data->member->getKey(),
+        ]);
+        $user->refresh();
+        $this->assertSame($otherOrganization->getKey(), $user->currentOrganization->getKey());
+        Event::assertDispatched(function (MemberRemoved $event) use ($data): bool {
+            return $event->organization->is($data->organization) &&
+                $event->member->is($data->member);
+        }, 1);
+    }
+
+    public function test_destroy_endpoint_creates_new_organization_and_sets_the_current_organization_to_it_if_user_is_not_member_of_any_other_organization(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:delete',
+        ]);
+        $organization = $data->organization;
+        $user = $data->user;
+        Passport::actingAs($user);
+        Event::fake([
+            MemberRemoved::class,
+        ]);
+        $this->assertDatabaseCount(Organization::class, 1);
+
+        // Act
+        $response = $this->deleteJson(route('api.v1.members.destroy', [$data->organization->getKey(), $data->member->getKey()]));
+
+        // Assert
+        $response->assertStatus(204);
+        $this->assertDatabaseCount(Organization::class, 2);
+        $newOrganization = Organization::where('id', '!=', $organization->getKey())->first();
+        $this->assertNotNull($newOrganization);
+        $this->assertDatabaseMissing(Member::class, [
+            'id' => $data->member->getKey(),
+        ]);
+        $this->assertDatabaseHas(Member::class, [
+            'organization_id' => $newOrganization->getKey(),
+            'user_id' => $user->getKey(),
+        ]);
+        $user->refresh();
+        $this->assertNotNull($user->currentOrganization);
+        Event::assertDispatched(function (MemberRemoved $event) use ($data): bool {
+            return $event->organization->is($data->organization) &&
+                $event->member->is($data->member);
+        }, 1);
+    }
+
     public function test_destroy_endpoint_succeeds_if_member_is_still_in_use_by_a_project_member_and_delete_related_is_active(): void
     {
         // Arrange
@@ -937,6 +1035,37 @@ class MemberEndpointTest extends ApiEndpointTestAbstract
         $response->assertForbidden();
     }
 
+    public function test_invite_placeholder_fails_if_there_is_already_an_invitation_with_the_same_email(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:invite-placeholder',
+            'invitations:create',
+        ]);
+        $placeholder = User::factory()->placeholder()->create([
+            'email' => 'user@mail.test',
+        ]);
+        $placeholderMember = Member::factory()->forUser($placeholder)->forOrganization($data->organization)->role(Role::Placeholder)->create();
+        OrganizationInvitation::factory()->forOrganization($data->organization)->create([
+            'email' => $placeholder->email,
+        ]);
+        Passport::actingAs($data->user);
+
+        // Act
+        $response = $this->postJson(route('api.v1.members.invite-placeholder', [
+            'organization' => $data->organization->id,
+            'member' => $placeholderMember->id,
+        ]));
+
+        // Assert
+        $response->assertStatus(400);
+        $response->assertExactJson([
+            'error' => true,
+            'key' => 'invitation_for_the_email_already_exists',
+            'message' => 'The email has already been invited to the organization. Please wait for the user to accept the invitation or resend the invitation email.',
+        ]);
+    }
+
     public function test_invite_placeholder_returns_400_if_user_is_not_placeholder(): void
     {
         // Arrange