app/Actions/Notifications/DeliverNotificationAction.php

@@ -2,17 +2,278 @@
 
 namespace App\Actions\Notifications;
 
+use App\Enums\NotificationChannel;
+use App\Enums\NotificationDeliveryStatus;
+use App\Models\NotificationAction;
+use App\Models\NotificationDeliveryLog;
+use Carbon\CarbonImmutable;
 use Illuminate\Contracts\Queue\ShouldQueue;
 use Illuminate\Foundation\Queue\Queueable;
+use Illuminate\Http\Client\ConnectionException;
+use Illuminate\Http\Client\Response;
+use Illuminate\Support\Facades\Http;
+use Illuminate\Support\Str;
+use Throwable;
 
 class DeliverNotificationAction implements ShouldQueue
 {
     use Queueable;
 
+    public int $tries = 3;
+
+    public int $timeout = 15;
+
     public function __construct(
         public int $notificationActionId,
         public TicketStatusChangedPayload $payload,
+        public ?int $notificationDeliveryLogId,
     ) {}
 
-    public function handle(): void {}
+    /**
+     * @return list<int>
+     */
+    public function backoff(): array
+    {
+        return [15, 60, 300];
+    }
+
+    public function handle(): void
+    {
+        $notificationAction = NotificationAction::query()->find($this->notificationActionId);
+
+        if ($notificationAction === null) {
+            return;
+        }
+
+        if ($notificationAction->channel !== NotificationChannel::Webhook) {
+            return;
+        }
+
+        $deliveryLog = $this->resolveDeliveryLog($notificationAction);
+        $attemptCount = $this->attempts();
+        $attemptedAt = CarbonImmutable::now();
+
+        try {
+            $response = Http::acceptJson()
+                ->asJson()
+                ->connectTimeout(5)
+                ->timeout(10)
+                ->post($notificationAction->delivery_url, $this->payload->toArray());
+        } catch (ConnectionException $exception) {
+            $this->handleConnectionFailure($deliveryLog, $attemptCount, $attemptedAt, $exception);
+
+            return;
+        }
+
+        if ($response->successful()) {
+            $this->markSucceeded($deliveryLog, $response, $attemptCount, $attemptedAt);
+
+            return;
+        }
+
+        if ($this->shouldRetry($response) && $this->hasAttemptsRemaining($attemptCount)) {
+            $this->markRetryable($deliveryLog, $response, $attemptCount, $attemptedAt);
+            $this->release($this->backoffDelay($attemptCount));
+
+            return;
+        }
+
+        $this->markFailed($deliveryLog, $response, $attemptCount, $attemptedAt);
+        $this->fail(new \RuntimeException($this->responseFailureDescription($response)));
+    }
+
+    public function failed(?Throwable $exception): void
+    {
+        $deliveryLog = $this->loadDeliveryLog();
+
+        if ($deliveryLog === null || $deliveryLog->delivery_status === NotificationDeliveryStatus::Succeeded) {
+            return;
+        }
+
+        $deliveryLog->update([
+            'attempt_count' => max($deliveryLog->attempt_count, $this->attempts()),
+            'delivery_status' => NotificationDeliveryStatus::Failed,
+            'delivered_at' => null,
+            'error_excerpt' => $deliveryLog->error_excerpt ?? $this->excerpt($exception?->getMessage()),
+            'last_attempted_at' => $deliveryLog->last_attempted_at ?? CarbonImmutable::now(),
+        ]);
+    }
+
+    private function handleConnectionFailure(
+        NotificationDeliveryLog $deliveryLog,
+        int $attemptCount,
+        CarbonImmutable $attemptedAt,
+        ConnectionException $exception,
+    ): void {
+        $errorExcerpt = $this->excerpt($exception->getMessage()) ?? 'Webhook request failed.';
+
+        if ($this->hasAttemptsRemaining($attemptCount)) {
+            $deliveryLog->update([
+                'attempt_count' => $attemptCount,
+                'delivery_status' => NotificationDeliveryStatus::Retryable,
+                'delivered_at' => null,
+                'error_excerpt' => $errorExcerpt,
+                'http_status' => null,
+                'last_attempted_at' => $attemptedAt,
+                'response_excerpt' => null,
+            ]);
+
+            $this->release($this->backoffDelay($attemptCount));
+
+            return;
+        }
+
+        $deliveryLog->update([
+            'attempt_count' => $attemptCount,
+            'delivery_status' => NotificationDeliveryStatus::Failed,
+            'delivered_at' => null,
+            'error_excerpt' => $errorExcerpt,
+            'http_status' => null,
+            'last_attempted_at' => $attemptedAt,
+            'response_excerpt' => null,
+        ]);
+
+        $this->fail($exception);
+    }
+
+    private function markSucceeded(
+        NotificationDeliveryLog $deliveryLog,
+        Response $response,
+        int $attemptCount,
+        CarbonImmutable $attemptedAt,
+    ): void {
+        $deliveryLog->update([
+            'attempt_count' => $attemptCount,
+            'delivery_status' => NotificationDeliveryStatus::Succeeded,
+            'delivered_at' => $attemptedAt,
+            'error_excerpt' => null,
+            'http_status' => $response->status(),
+            'last_attempted_at' => $attemptedAt,
+            'response_excerpt' => $this->responseExcerpt($response),
+        ]);
+    }
+
+    private function markRetryable(
+        NotificationDeliveryLog $deliveryLog,
+        Response $response,
+        int $attemptCount,
+        CarbonImmutable $attemptedAt,
+    ): void {
+        $deliveryLog->update([
+            'attempt_count' => $attemptCount,
+            'delivery_status' => NotificationDeliveryStatus::Retryable,
+            'delivered_at' => null,
+            'error_excerpt' => $this->responseFailureDescription($response),
+            'http_status' => $response->status(),
+            'last_attempted_at' => $attemptedAt,
+            'response_excerpt' => $this->responseExcerpt($response),
+        ]);
+    }
+
+    private function markFailed(
+        NotificationDeliveryLog $deliveryLog,
+        Response $response,
+        int $attemptCount,
+        CarbonImmutable $attemptedAt,
+    ): void {
+        $deliveryLog->update([
+            'attempt_count' => $attemptCount,
+            'delivery_status' => NotificationDeliveryStatus::Failed,
+            'delivered_at' => null,
+            'error_excerpt' => $this->responseFailureDescription($response),
+            'http_status' => $response->status(),
+            'last_attempted_at' => $attemptedAt,
+            'response_excerpt' => $this->responseExcerpt($response),
+        ]);
+    }
+
+    private function resolveDeliveryLog(NotificationAction $notificationAction): NotificationDeliveryLog
+    {
+        $deliveryLog = $this->loadDeliveryLog();
+
+        if ($deliveryLog !== null) {
+            return $deliveryLog;
+        }
+
+        $deliveryLog = NotificationDeliveryLog::query()->create([
+            'attempt_count' => 0,
+            'channel' => $notificationAction->channel,
+            'delivery_status' => NotificationDeliveryStatus::Pending,
+            'event_type' => $this->payload->eventType,
+            'notification_action_id' => $notificationAction->id,
+            'payload_metadata' => $this->payloadMetadata(),
+        ]);
+
+        $this->notificationDeliveryLogId = $deliveryLog->id;
+
+        return $deliveryLog;
+    }
+
+    private function loadDeliveryLog(): ?NotificationDeliveryLog
+    {
+        if ($this->notificationDeliveryLogId === null) {
+            return null;
+        }
+
+        return NotificationDeliveryLog::query()
+            ->whereKey($this->notificationDeliveryLogId)
+            ->where('notification_action_id', $this->notificationActionId)
+            ->first();
+    }
+
+    private function shouldRetry(Response $response): bool
+    {
+        return $response->serverError() || in_array($response->status(), [408, 429], true);
+    }
+
+    private function hasAttemptsRemaining(int $attemptCount): bool
+    {
+        return $attemptCount < $this->tries;
+    }
+
+    private function backoffDelay(int $attemptCount): int
+    {
+        $backoff = $this->backoff();
+        $index = min($attemptCount - 1, count($backoff) - 1);
+
+        return $backoff[$index];
+    }
+
+    private function responseExcerpt(Response $response): ?string
+    {
+        return $this->excerpt($response->body()) ?? $this->excerpt($response->reason());
+    }
+
+    private function responseFailureDescription(Response $response): string
+    {
+        $reason = $this->excerpt($response->reason());
+
+        if ($reason === null) {
+            return "Webhook returned HTTP {$response->status()}.";
+        }
+
+        return "Webhook returned HTTP {$response->status()} {$reason}.";
+    }
+
+    /**
+     * @return array{project_key: string, ticket_key: string}
+     */
+    private function payloadMetadata(): array
+    {
+        return [
+            'project_key' => $this->payload->projectKey,
+            'ticket_key' => $this->payload->ticketKey,
+        ];
+    }
+
+    private function excerpt(?string $value): ?string
+    {
+        if ($value === null) {
+            return null;
+        }
+
+        $excerpt = (string) Str::of($value)->trim()->squish()->limit(500);
+
+        return $excerpt === '' ? null : $excerpt;
+    }
 }

app/Actions/Notifications/QueueTicketStatusChangedNotificationDeliveries.php

@@ -2,7 +2,10 @@
 
 namespace App\Actions\Notifications;
 
+use App\Enums\NotificationChannel;
+use App\Enums\NotificationDeliveryStatus;
 use App\Models\NotificationAction;
+use App\Models\NotificationDeliveryLog;
 
 class QueueTicketStatusChangedNotificationDeliveries
 {
@@ -12,11 +15,28 @@ class QueueTicketStatusChangedNotificationDeliveries
             ->enabled()
             ->where('project_id', $event->payload->projectId)
             ->where('event_type', $event->payload->eventType->value)
-            ->get(['id'])
+            ->get(['channel', 'id'])
             ->each(function (NotificationAction $notificationAction) use ($event): void {
+                $notificationDeliveryLogId = null;
+
+                if ($notificationAction->channel === NotificationChannel::Webhook) {
+                    $notificationDeliveryLogId = NotificationDeliveryLog::query()->create([
+                        'attempt_count' => 0,
+                        'channel' => $notificationAction->channel,
+                        'delivery_status' => NotificationDeliveryStatus::Pending,
+                        'event_type' => $event->payload->eventType,
+                        'notification_action_id' => $notificationAction->id,
+                        'payload_metadata' => [
+                            'project_key' => $event->payload->projectKey,
+                            'ticket_key' => $event->payload->ticketKey,
+                        ],
+                    ])->id;
+                }
+
                 DeliverNotificationAction::dispatch(
-                    $notificationAction->id,
+                    notificationActionId: $notificationAction->id,
-                    $event->payload,
+                    payload: $event->payload,
+                    notificationDeliveryLogId: $notificationDeliveryLogId,
                 );
             });
     }

tests/Feature/Notifications/DeliverNotificationActionTest.php

@@ -0,0 +1,300 @@
+<?php
+
+namespace Tests\Feature\Notifications;
+
+use App\Actions\Notifications\DeliverNotificationAction;
+use App\Actions\Notifications\TicketStatusChangedPayload;
+use App\Enums\NotificationDeliveryStatus;
+use App\Enums\NotificationEventType;
+use App\Models\NotificationAction;
+use App\Models\NotificationDeliveryLog;
+use Carbon\CarbonImmutable;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Http\Client\Request;
+use Illuminate\Support\Facades\Http;
+use Tests\TestCase;
+
+class DeliverNotificationActionTest extends TestCase
+{
+    use RefreshDatabase;
+
+    /**
+     * Ensure generic webhook deliveries send JSON payloads and mark successful log entries.
+     */
+    public function test_webhook_delivery_posts_structured_json_payload_and_marks_the_log_as_succeeded(): void
+    {
+        Http::preventStrayRequests();
+        Http::fake([
+            'https://hooks.example.test/kanbangit/ticket-status' => Http::response('', 204),
+        ]);
+
+        $notificationAction = NotificationAction::factory()->webhook()->create([
+            'delivery_url' => 'https://hooks.example.test/kanbangit/ticket-status',
+        ]);
+        $deliveryLog = $this->createPendingDeliveryLog($notificationAction);
+
+        (new DeliverNotificationAction(
+            notificationActionId: $notificationAction->id,
+            payload: $this->payload(),
+            notificationDeliveryLogId: $deliveryLog->id,
+        ))->handle();
+
+        Http::assertSentCount(1);
+        Http::assertSent(function (Request $request): bool {
+            return $request->method() === 'POST'
+                && $request->url() === 'https://hooks.example.test/kanbangit/ticket-status'
+                && $request->hasHeader('Accept', 'application/json')
+                && $request->hasHeader('Content-Type', 'application/json')
+                && $request->data() === $this->expectedPayload();
+        });
+
+        $deliveryLog = $deliveryLog->fresh();
+
+        $this->assertSame(NotificationDeliveryStatus::Succeeded, $deliveryLog->delivery_status);
+        $this->assertSame(1, $deliveryLog->attempt_count);
+        $this->assertSame(204, $deliveryLog->http_status);
+        $this->assertSame('No Content', $deliveryLog->response_excerpt);
+        $this->assertNull($deliveryLog->error_excerpt);
+        $this->assertNotNull($deliveryLog->last_attempted_at);
+        $this->assertNotNull($deliveryLog->delivered_at);
+    }
+
+    /**
+     * Ensure retryable webhook responses release the job and update the delivery log.
+     */
+    public function test_retryable_webhook_responses_mark_the_log_retryable_and_release_the_job(): void
+    {
+        Http::preventStrayRequests();
+        Http::fake([
+            'https://hooks.example.test/kanbangit/ticket-status' => Http::response([
+                'message' => 'Temporary outage',
+            ], 503),
+        ]);
+
+        $notificationAction = NotificationAction::factory()->webhook()->create([
+            'delivery_url' => 'https://hooks.example.test/kanbangit/ticket-status',
+        ]);
+        $deliveryLog = $this->createPendingDeliveryLog($notificationAction);
+        $job = (new DeliverNotificationAction(
+            notificationActionId: $notificationAction->id,
+            payload: $this->payload(),
+            notificationDeliveryLogId: $deliveryLog->id,
+        ))->withFakeQueueInteractions();
+
+        $job->handle();
+
+        $job->assertReleased($job->backoff()[0]);
+        $job->assertNotFailed();
+
+        $deliveryLog = $deliveryLog->fresh();
+
+        $this->assertSame(NotificationDeliveryStatus::Retryable, $deliveryLog->delivery_status);
+        $this->assertSame(1, $deliveryLog->attempt_count);
+        $this->assertSame(503, $deliveryLog->http_status);
+        $this->assertStringContainsString('Temporary outage', (string) $deliveryLog->response_excerpt);
+        $this->assertSame('Webhook returned HTTP 503 Service Unavailable.', $deliveryLog->error_excerpt);
+        $this->assertNull($deliveryLog->delivered_at);
+    }
+
+    /**
+     * Ensure permanent webhook errors fail immediately without scheduling another retry.
+     */
+    public function test_permanent_webhook_responses_mark_the_log_as_failed(): void
+    {
+        Http::preventStrayRequests();
+        Http::fake([
+            'https://hooks.example.test/kanbangit/ticket-status' => Http::response([
+                'message' => 'The ticket payload was invalid.',
+            ], 422),
+        ]);
+
+        $notificationAction = NotificationAction::factory()->webhook()->create([
+            'delivery_url' => 'https://hooks.example.test/kanbangit/ticket-status',
+        ]);
+        $deliveryLog = $this->createPendingDeliveryLog($notificationAction);
+        $job = (new DeliverNotificationAction(
+            notificationActionId: $notificationAction->id,
+            payload: $this->payload(),
+            notificationDeliveryLogId: $deliveryLog->id,
+        ))->withFakeQueueInteractions();
+
+        $job->handle();
+
+        $job->assertFailed();
+        $job->assertNotReleased();
+
+        $deliveryLog = $deliveryLog->fresh();
+
+        $this->assertSame(NotificationDeliveryStatus::Failed, $deliveryLog->delivery_status);
+        $this->assertSame(1, $deliveryLog->attempt_count);
+        $this->assertSame(422, $deliveryLog->http_status);
+        $this->assertStringContainsString('invalid', (string) $deliveryLog->response_excerpt);
+        $this->assertStringContainsString('Webhook returned HTTP 422', (string) $deliveryLog->error_excerpt);
+    }
+
+    /**
+     * Ensure connection failures are marked retryable while attempts remain.
+     */
+    public function test_connection_failures_mark_the_log_retryable_and_release_the_job(): void
+    {
+        Http::preventStrayRequests();
+        Http::fake([
+            'https://hooks.example.test/kanbangit/ticket-status' => Http::failedConnection(
+                'Connection timed out while contacting the remote endpoint.',
+            ),
+        ]);
+
+        $notificationAction = NotificationAction::factory()->webhook()->create([
+            'delivery_url' => 'https://hooks.example.test/kanbangit/ticket-status',
+        ]);
+        $deliveryLog = $this->createPendingDeliveryLog($notificationAction);
+        $job = (new DeliverNotificationAction(
+            notificationActionId: $notificationAction->id,
+            payload: $this->payload(),
+            notificationDeliveryLogId: $deliveryLog->id,
+        ))->withFakeQueueInteractions();
+
+        $job->handle();
+
+        $job->assertReleased($job->backoff()[0]);
+        $job->assertNotFailed();
+
+        $deliveryLog = $deliveryLog->fresh();
+
+        $this->assertSame(NotificationDeliveryStatus::Retryable, $deliveryLog->delivery_status);
+        $this->assertSame(1, $deliveryLog->attempt_count);
+        $this->assertNull($deliveryLog->http_status);
+        $this->assertNull($deliveryLog->response_excerpt);
+        $this->assertSame('Connection timed out while contacting the remote endpoint.', $deliveryLog->error_excerpt);
+    }
+
+    /**
+     * Ensure the last retryable attempt is marked failed once the job exhausts its retries.
+     */
+    public function test_final_retryable_failures_mark_the_log_as_failed(): void
+    {
+        Http::preventStrayRequests();
+        Http::fake([
+            'https://hooks.example.test/kanbangit/ticket-status' => Http::response([
+                'message' => 'Webhook service unavailable',
+            ], 503),
+        ]);
+
+        $notificationAction = NotificationAction::factory()->webhook()->create([
+            'delivery_url' => 'https://hooks.example.test/kanbangit/ticket-status',
+        ]);
+        $deliveryLog = $this->createPendingDeliveryLog($notificationAction);
+        $job = (new DeliverNotificationAction(
+            notificationActionId: $notificationAction->id,
+            payload: $this->payload(),
+            notificationDeliveryLogId: $deliveryLog->id,
+        ))->withFakeQueueInteractions();
+
+        $job->job->attempts = $job->tries;
+
+        $job->handle();
+
+        $job->assertFailed();
+        $job->assertNotReleased();
+
+        $deliveryLog = $deliveryLog->fresh();
+
+        $this->assertSame(NotificationDeliveryStatus::Failed, $deliveryLog->delivery_status);
+        $this->assertSame($job->tries, $deliveryLog->attempt_count);
+        $this->assertSame(503, $deliveryLog->http_status);
+        $this->assertSame('Webhook returned HTTP 503 Service Unavailable.', $deliveryLog->error_excerpt);
+    }
+
+    /**
+     * Ensure webhook delivery jobs expose the retry and timeout configuration required by the ticket.
+     */
+    public function test_webhook_delivery_jobs_use_the_expected_retry_and_backoff_configuration(): void
+    {
+        $job = new DeliverNotificationAction(
+            notificationActionId: 1,
+            payload: $this->payload(),
+            notificationDeliveryLogId: 1,
+        );
+
+        $this->assertSame(3, $job->tries);
+        $this->assertSame(15, $job->timeout);
+        $this->assertSame([15, 60, 300], $job->backoff());
+    }
+
+    private function createPendingDeliveryLog(NotificationAction $notificationAction): NotificationDeliveryLog
+    {
+        return NotificationDeliveryLog::factory()
+            ->pending()
+            ->forNotificationAction($notificationAction)
+            ->create([
+                'payload_metadata' => [
+                    'project_key' => 'CORE',
+                    'ticket_key' => 'CORE-42',
+                ],
+            ]);
+    }
+
+    private function payload(): TicketStatusChangedPayload
+    {
+        return new TicketStatusChangedPayload(
+            eventType: NotificationEventType::TicketStatusChanged,
+            projectId: 10,
+            projectKey: 'CORE',
+            projectName: 'Core Platform',
+            ticketId: 42,
+            ticketKey: 'CORE-42',
+            ticketTitle: 'Fix webhook delivery',
+            ticketUrl: 'https://kanbangit.test/projects/core/tickets/42',
+            actorId: 7,
+            actorName: 'Erica Example',
+            fromStatusId: 1,
+            fromStatusLabel: 'Backlog',
+            toStatusId: 2,
+            toStatusLabel: 'Doing',
+            occurredAt: CarbonImmutable::parse('2026-04-24T09:15:30+00:00'),
+        );
+    }
+
+    /**
+     * @return array{
+     *     event_type: string,
+     *     project: array{id: int, key: string, name: string},
+     *     ticket: array{id: int, key: string, title: string},
+     *     actor: array{id: int, name: string},
+     *     from: array{id: int, label: string},
+     *     to: array{id: int, label: string},
+     *     ticket_url: string,
+     *     occurred_at: string
+     * }
+     */
+    private function expectedPayload(): array
+    {
+        return [
+            'event_type' => 'ticket_status_changed',
+            'project' => [
+                'id' => 10,
+                'key' => 'CORE',
+                'name' => 'Core Platform',
+            ],
+            'ticket' => [
+                'id' => 42,
+                'key' => 'CORE-42',
+                'title' => 'Fix webhook delivery',
+            ],
+            'actor' => [
+                'id' => 7,
+                'name' => 'Erica Example',
+            ],
+            'from' => [
+                'id' => 1,
+                'label' => 'Backlog',
+            ],
+            'to' => [
+                'id' => 2,
+                'label' => 'Doing',
+            ],
+            'ticket_url' => 'https://kanbangit.test/projects/core/tickets/42',
+            'occurred_at' => '2026-04-24T09:15:30.000000Z',
+        ];
+    }
+}

tests/Feature/Notifications/TicketStatusChangedNotificationDispatchTest.php

@@ -5,6 +5,7 @@ namespace Tests\Feature\Notifications;
 use App\Actions\Notifications\DeliverNotificationAction;
 use App\Actions\ProjectTicketMetadata\InitializeProjectTicketMetadata;
 use App\Enums\NotificationChannel;
+use App\Enums\NotificationDeliveryStatus;
 use App\Enums\NotificationEventType;
 use App\Models\BoardColumn;
 use App\Models\NotificationAction;
@@ -16,6 +17,7 @@ use App\Models\User;
 use Carbon\CarbonImmutable;
 use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Facades\DB;
+use Illuminate\Support\Facades\Http;
 use Illuminate\Support\Facades\Queue;
 use Tests\TestCase;
 
@@ -166,6 +168,86 @@ class TicketStatusChangedNotificationDispatchTest extends TestCase
         $this->assertDatabaseCount('ticket_worklog_entries', 0);
     }
 
+    /**
+     * Ensure ticket moves stay successful even when webhook delivery fails later on a queued attempt.
+     */
+    public function test_ticket_moves_still_succeed_when_webhook_delivery_fails_later(): void
+    {
+        Queue::fake();
+        Http::preventStrayRequests();
+
+        $user = User::factory()->create([
+            'name' => 'Erica Example',
+        ]);
+        $project = Project::factory()->create([
+            'key' => 'CORE',
+        ]);
+
+        app(InitializeProjectTicketMetadata::class)->handle($project);
+
+        $doingColumn = BoardColumn::factory()->for($project)->create([
+            'name' => 'Doing',
+            'position' => 1,
+        ]);
+        $doingStatus = $this->createColumnStatus($doingColumn);
+        $backlogStatus = $this->backlogStatus($project);
+        $this->allowMove($backlogStatus, $doingStatus);
+
+        $ticket = $this->createTicket($project, $backlogStatus, 'Retry failing webhook');
+        $webhookAction = NotificationAction::factory()
+            ->webhook()
+            ->for($project)
+            ->create([
+                'delivery_url' => 'https://hooks.example.test/kanbangit/retry-failing-webhook',
+            ]);
+
+        $this->syncProjectPermissions($project, $user, ['edit', 'view']);
+
+        $this->actingAs($user)
+            ->patch(route('projects.tickets.status.update', [$project, $ticket]), [
+                'redirect_to' => 'backlog',
+                'ticket_status_id' => $doingStatus->id,
+            ])
+            ->assertRedirect(route('projects.backlog.index', $project))
+            ->assertSessionHas('status', 'CORE-1 moved to Doing.');
+
+        $queuedJob = null;
+
+        Queue::assertPushed(DeliverNotificationAction::class, function (DeliverNotificationAction $job) use ($webhookAction, &$queuedJob): bool {
+            if ($job->notificationActionId !== $webhookAction->id) {
+                return false;
+            }
+
+            $queuedJob = $job;
+
+            return true;
+        });
+
+        $this->assertInstanceOf(DeliverNotificationAction::class, $queuedJob);
+
+        Http::fake([
+            'https://hooks.example.test/kanbangit/retry-failing-webhook' => Http::failedConnection(
+                'Connection timed out while contacting the remote endpoint.',
+            ),
+        ]);
+
+        $queuedJob->withFakeQueueInteractions()->handle();
+
+        $queuedJob->assertReleased($queuedJob->backoff()[0]);
+
+        $this->assertDatabaseHas('tickets', [
+            'id' => $ticket->id,
+            'ticket_status_id' => $doingStatus->id,
+        ]);
+
+        $this->assertDatabaseHas('notification_delivery_logs', [
+            'notification_action_id' => $webhookAction->id,
+            'delivery_status' => NotificationDeliveryStatus::Retryable->value,
+            'attempt_count' => 1,
+            'http_status' => null,
+        ]);
+    }
+
     private function backlogStatus(Project $project): TicketStatus
     {
         return $project->ticketStatuses()