diff --git a/app/Jobs/DockerCleanupJob.php b/app/Jobs/DockerCleanupJob.php
index 6730e7a976..1a338f093f 100644
--- a/app/Jobs/DockerCleanupJob.php
+++ b/app/Jobs/DockerCleanupJob.php
@@ -16,6 +16,7 @@ use Illuminate\Contracts\Queue\ShouldQueue;
 use Illuminate\Foundation\Bus\Dispatchable;
 use Illuminate\Queue\InteractsWithQueue;
 use Illuminate\Queue\SerializesModels;
+use Illuminate\Support\Facades\Cache;
 
 class DockerCleanupJob implements ShouldBeEncrypted, ShouldQueue
 {
@@ -95,6 +96,7 @@ class DockerCleanupJob implements ShouldBeEncrypted, ShouldQueue
             $this->execution_log = DockerCleanupExecution::create([
                 'server_id' => $this->server->id,
             ]);
+            $this->rememberExecution();
 
             if (! $this->server->isFunctional()) {
                 $this->execution_log->update([
@@ -204,21 +206,41 @@ class DockerCleanupJob implements ShouldBeEncrypted, ShouldQueue
                     'finished_at' => Carbon::now()->toImmutable(),
                 ]);
             }
+
+            if (! $failed && $this->executionCacheKey()) {
+                Cache::forget($this->executionCacheKey());
+            }
         }
     }
 
+    /**
+     * failed() runs on a fresh job copy built from the queue payload (for example after a worker timeout),
+     * so the execution this run created is kept under the queue job uuid instead of on the job.
+     */
+    private function rememberExecution(): void
+    {
+        if ($this->executionCacheKey()) {
+            Cache::put($this->executionCacheKey(), $this->execution_log->id, now()->addSeconds((int) config('queue.connections.redis.retry_after', 86400) + 3600));
+        }
+    }
+
+    private function executionCacheKey(): ?string
+    {
+        $jobUuid = $this->job?->uuid();
+
+        return $jobUuid ? 'docker-cleanup-execution:'.$jobUuid : null;
+    }
+
     public function failed(?\Throwable $exception): void
     {
         if ($this->occurrenceUuid) {
             app(ScheduledJobDeliveryService::class)->fail($this->occurrenceUuid, $this->job?->uuid() ?? $this->occurrenceUuid);
         }
 
-        $execution = DockerCleanupExecution::query()
-            ->where('server_id', $this->server->id)
-            ->where('status', 'running')
-            ->whereNull('finished_at')
-            ->latest('id')
-            ->first();
+        // Only this run's own execution. A run that never started (e.g. a manual run whose wait for the
+        // server lock ran out) created none and must not fail another running cleanup.
+        $executionId = $this->executionCacheKey() ? Cache::pull($this->executionCacheKey()) : null;
+        $execution = $executionId ? DockerCleanupExecution::query()->find($executionId) : null;
 
         if (! $execution) {
             return;
diff --git a/tests/Feature/DockerCleanupJobTest.php b/tests/Feature/DockerCleanupJobTest.php
index 37cafbd54d..31b12bb7ac 100644
--- a/tests/Feature/DockerCleanupJobTest.php
+++ b/tests/Feature/DockerCleanupJobTest.php
@@ -19,6 +19,8 @@ use App\Services\ScheduledJobDeliveryService;
 use App\Support\Actions\UniqueUntilProcessingJobDecorator;
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Queue\Jobs\FakeJob;
+use Illuminate\Queue\MaxAttemptsExceededException;
 use Illuminate\Support\Carbon;
 use Illuminate\Support\Collection;
 use Illuminate\Support\Facades\Artisan;
@@ -134,26 +136,63 @@ it('creates a failed execution record when server is force disabled', function (
         ->and($execution->message)->toContain('not functional');
 });
 
-it('finishes the latest running execution when the job fails after a timeout', function () {
-    $user = User::factory()->create();
-    $team = $user->teams()->first();
-    $server = Server::factory()->create(['team_id' => $team->id]);
+function dockerCleanupQueueJob(string $uuid): FakeJob
+{
+    return new class($uuid) extends FakeJob
+    {
+        public function __construct(private string $jobUuid) {}
 
-    $olderExecution = DockerCleanupExecution::create([
-        'server_id' => $server->id,
-    ]);
-    $timedOutExecution = DockerCleanupExecution::create([
-        'server_id' => $server->id,
-    ]);
+        public function getRawBody()
+        {
+            return json_encode(['uuid' => $this->jobUuid]);
+        }
+    };
+}
 
-    $job = new DockerCleanupJob($server);
-    $job->failed(new RuntimeException('Docker cleanup job has timed out.'));
+it('finishes its own execution when the job fails after a timeout, not a newer running cleanup', function () {
+    Notification::fake();
+    Event::fake([DockerCleanupDone::class]);
+    $server = dockerCleanupReachableServer();
+    $queueJob = dockerCleanupQueueJob('prr-fix-timed-out-cleanup');
+    $statesWhenTimedOut = null;
+    dockerCleanupFakeProcesses(function () use ($server, $queueJob, &$statesWhenTimedOut) {
+        if ($statesWhenTimedOut !== null) {
+            return;
+        }
+        $ownExecution = DockerCleanupExecution::query()->sole();
+        $scheduledExecution = DockerCleanupExecution::create(['server_id' => $server->id]);
 
-    expect($timedOutExecution->refresh()->status)->toBe('failed')
-        ->and($timedOutExecution->message)->toBe('Docker cleanup job has timed out.')
-        ->and($timedOutExecution->finished_at)->not->toBeNull()
-        ->and($olderExecution->refresh()->status)->toBe('running')
-        ->and($olderExecution->finished_at)->toBeNull();
+        // The worker timeout calls failed() on a fresh job copy built from the same queue payload.
+        (new DockerCleanupJob($server, true))->setJob($queueJob)->failed(new RuntimeException('Docker cleanup job has timed out.'));
+
+        $statesWhenTimedOut = [
+            'own' => $ownExecution->fresh()->only(['status', 'message']),
+            'ownFinished' => $ownExecution->fresh()->finished_at !== null,
+            'scheduled' => $scheduledExecution->fresh()->only(['status', 'finished_at']),
+        ];
+    });
+
+    (new DockerCleanupJob($server, true))->setJob($queueJob)->handle();
+
+    expect($statesWhenTimedOut['own'])->toBe(['status' => 'failed', 'message' => 'Docker cleanup job has timed out.'])
+        ->and($statesWhenTimedOut['ownFinished'])->toBeTrue()
+        ->and($statesWhenTimedOut['scheduled'])->toBe(['status' => 'running', 'finished_at' => null]);
+});
+
+it('leaves a running scheduled cleanup untouched when a manual cleanup fails before it started', function () {
+    Notification::fake();
+    Event::fake([DockerCleanupDone::class]);
+    $server = dockerCleanupReachableServer();
+    $scheduledExecution = DockerCleanupExecution::create(['server_id' => $server->id]);
+
+    (new DockerCleanupJob($server, true))
+        ->setJob(dockerCleanupQueueJob('prr-fix-waiting-manual-cleanup'))
+        ->failed(new MaxAttemptsExceededException('App\Jobs\DockerCleanupJob has been attempted too many times.'));
+
+    expect($scheduledExecution->fresh()->status)->toBe('running')
+        ->and($scheduledExecution->fresh()->finished_at)->toBeNull();
+    Notification::assertNothingSent();
+    Event::assertNotDispatched(DockerCleanupDone::class);
 });
 
 it('skips a scheduled cleanup occurrence while another cleanup holds the server lock, so it is not reported missed later', function () {