diff --git a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowCronJob.php b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowCronJob.php
index cb6f1c971..786bae3c9 100644
--- a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowCronJob.php
+++ b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowCronJob.php
@@ -54,8 +54,8 @@ class CancelStaleWorkflowCronJob implements CronJobInterface
 
         foreach ($staleWorkflowIds as $wId) {
             try {
-                $this->messageBus->dispatch(new CancelStaleWorkflow($wId));
-                $lastCanceled = $wId;
+                $this->messageBus->dispatch(new CancelStaleWorkflowMessage($wId));
+                $lastCanceled = max($wId, $lastCanceled);
                 ++$processedCount;
             } catch (\Exception $e) {
                 $this->logger->error("Failed to dispatch CancelStaleWorkflow for ID {$wId}", ['exception' => $e]);
diff --git a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowHandler.php b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowHandler.php
index 533283a59..a3eefb193 100644
--- a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowHandler.php
+++ b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowHandler.php
@@ -14,6 +14,7 @@ namespace Chill\MainBundle\Service\Workflow;
 use Chill\MainBundle\Repository\Workflow\EntityWorkflowRepository;
 use Doctrine\ORM\EntityManagerInterface;
 use Psr\Log\LoggerInterface;
+use Symfony\Component\Clock\ClockInterface;
 use Symfony\Component\Messenger\Attribute\AsMessageHandler;
 use Symfony\Component\Messenger\Exception\UnrecoverableMessageHandlingException;
 use Symfony\Component\Workflow\Registry;
@@ -21,13 +22,29 @@ use Symfony\Component\Workflow\Registry;
 #[AsMessageHandler]
 class CancelStaleWorkflowHandler
 {
-    public function __construct(private readonly EntityWorkflowRepository $workflowRepository, private readonly Registry $registry, private EntityManagerInterface $em, private LoggerInterface $logger) {}
+    public const string KEEP_INTERVAL = 'P90D';
 
-    public function __invoke(CancelStaleWorkflow $message): void
+    public function __construct(private readonly EntityWorkflowRepository $workflowRepository, private readonly Registry $registry, private readonly EntityManagerInterface $em, private readonly LoggerInterface $logger, private readonly ClockInterface $clock) {}
+
+    public function __invoke(CancelStaleWorkflowMessage $message): void
     {
         $workflowId = $message->getWorkflowId();
 
+        $olderThanDate = $this->clock->now()->sub(new \DateInterval(self::KEEP_INTERVAL));
+        $staleWorkflows = $this->workflowRepository->findWorkflowsWithoutFinalStepAndOlderThan($olderThanDate);
+
         $workflow = $this->workflowRepository->find($workflowId);
+
+        if (in_array($workflow, $staleWorkflows, true)) {
+            $this->logger->alert('Workflow has transitioned in the meantime.', [$workflowId]);
+            return;
+        }
+
+        if (null === $workflow) {
+            $this->logger->alert('Workflow was not found!', [$workflowId]);
+            return;
+        }
+
         $workflowComponent = $this->registry->get($workflow, $workflow->getWorkflowName());
         $metadataStore = $workflowComponent->getMetadataStore();
         $transitions = $workflowComponent->getEnabledTransitions($workflow);
@@ -44,15 +61,15 @@ class CancelStaleWorkflowHandler
                 $isFinalPositive = $metadataStore->getMetadata('isFinalPositive', $transition);
 
                 if ($isFinal && !$isFinalPositive) {
-                    $workflowComponent->apply($workflow, 'annule');
-                    $this->logger->info(sprintf('EntityWorkflow %d has been transitioned.', $workflowId));
+                    $workflowComponent->apply($workflow, $transition->getName());
+                    $this->logger->info('EntityWorkflow has been cancelled automatically.', [$workflowId]);
                     $transitionApplied = true;
                     break;
                 }
             }
 
             if (!$transitionApplied) {
-                $this->logger->error(sprintf('No valid transition found for EntityWorkflow %d.', $workflowId));
+                $this->logger->error('No valid transition found for EntityWorkflow %d.', [$workflowId]);
                 throw new UnrecoverableMessageHandlingException(sprintf('No valid transition found for EntityWorkflow %d.', $workflowId));
             }
         }
diff --git a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflow.php b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowMessage.php
similarity index 92%
rename from src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflow.php
rename to src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowMessage.php
index 118b9f57e..30d2b6ab8 100644
--- a/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflow.php
+++ b/src/Bundle/ChillMainBundle/Service/Workflow/CancelStaleWorkflowMessage.php
@@ -11,7 +11,7 @@ declare(strict_types=1);
 
 namespace Chill\MainBundle\Service\Workflow;
 
-class CancelStaleWorkflow
+class CancelStaleWorkflowMessage
 {
     public function __construct(public int $workflowId) {}
 
diff --git a/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowCronJobTest.php b/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowCronJobTest.php
index b56faf79b..f433e8b48 100644
--- a/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowCronJobTest.php
+++ b/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowCronJobTest.php
@@ -15,6 +15,10 @@ use Chill\MainBundle\Entity\CronJobExecution;
 use Chill\MainBundle\Repository\Workflow\EntityWorkflowRepository;
 use Chill\MainBundle\Service\Workflow\CancelStaleWorkflow;
 use Chill\MainBundle\Service\Workflow\CancelStaleWorkflowCronJob;
+use Chill\MainBundle\Service\Workflow\CancelStaleWorkflowMessage;
+use DateInvalidTimeZoneException;
+use DateMalformedStringException;
+use DateTimeImmutable;
 use Doctrine\DBAL\Connection;
 use PHPUnit\Framework\MockObject\Exception;
 use Psr\Log\LoggerInterface;
@@ -43,7 +47,7 @@ class CancelStaleWorkflowCronJobTest extends KernelTestCase
      */
     public function testCanRun(?CronJobExecution $cronJobExecution, bool $expected): void
     {
-        $clock = new MockClock(new \DateTimeImmutable('2024-01-01 00:00:00', new \DateTimeZone('+00:00')));
+        $clock = new MockClock(new DateTimeImmutable('2024-01-01 00:00:00', new \DateTimeZone('+00:00')));
         $logger = $this->createMock(LoggerInterface::class);
 
         $cronJob = new CancelStaleWorkflowCronJob($this->createMock(EntityWorkflowRepository::class), $clock, $this->buildMessageBus(), $logger);
@@ -52,17 +56,17 @@ class CancelStaleWorkflowCronJobTest extends KernelTestCase
     }
 
     /**
-     * @throws \DateMalformedStringException
-     * @throws \DateInvalidTimeZoneException
-     * @throws Exception
+     * @throws DateMalformedStringException
+     * @throws DateInvalidTimeZoneException
+     * @throws \Exception|Exception
      */
     public function testRun(): void
     {
-        $clock = new MockClock((new \DateTimeImmutable('now', new \DateTimeZone('+00:00')))->add(new \DateInterval('P120D')));
+        $clock = new MockClock((new DateTimeImmutable('now', new \DateTimeZone('+00:00')))->add(new \DateInterval('P120D')));
         $workflowRepository = $this->createMock(EntityWorkflowRepository::class);
         $logger = $this->createMock(LoggerInterface::class);
 
-        $workflowRepository->method('findWorkflowsWithoutFinalStepAndOlderThan')->willReturn([1, 2, 3]);
+        $workflowRepository->method('findWorkflowsWithoutFinalStepAndOlderThan')->willReturn([1, 3, 2]);
         $messageBus = $this->buildMessageBus(true);
 
         $cronJob = new CancelStaleWorkflowCronJob($workflowRepository, $clock, $messageBus, $logger);
@@ -80,17 +84,17 @@ class CancelStaleWorkflowCronJobTest extends KernelTestCase
     public static function buildTestCanRunData(): iterable
     {
         yield [
-            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new \DateTimeImmutable('2023-12-31 00:00:00', new \DateTimeZone('+00:00'))),
+            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new DateTimeImmutable('2023-12-31 00:00:00', new \DateTimeZone('+00:00'))),
             true,
         ];
 
         yield [
-            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new \DateTimeImmutable('2023-12-30 23:59:59', new \DateTimeZone('+00:00'))),
+            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new DateTimeImmutable('2023-12-30 23:59:59', new \DateTimeZone('+00:00'))),
             true,
         ];
 
         yield [
-            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new \DateTimeImmutable('2023-12-31 00:00:01', new \DateTimeZone('+00:00'))),
+            (new CronJobExecution('last-canceled-workflow-id'))->setLastEnd(new DateTimeImmutable('2023-12-31 00:00:01', new \DateTimeZone('+00:00'))),
             false,
         ];
     }
@@ -104,7 +108,7 @@ class CancelStaleWorkflowCronJobTest extends KernelTestCase
             false => $messageBus->method('dispatch'),
         };
 
-        $methodDispatch->willReturnCallback(function (CancelStaleWorkflow $message) {
+        $methodDispatch->willReturnCallback(function (CancelStaleWorkflowMessage $message) {
             return new Envelope($message);
         });
 
diff --git a/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowHandlerTest.php b/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowHandlerTest.php
index f7887a6cd..dbf88098f 100644
--- a/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowHandlerTest.php
+++ b/src/Bundle/ChillMainBundle/Tests/Services/Workflow/CancelStaleWorkflowHandlerTest.php
@@ -16,6 +16,7 @@ use Chill\MainBundle\Entity\Workflow\EntityWorkflowStep;
 use Chill\MainBundle\Repository\Workflow\EntityWorkflowRepository;
 use Chill\MainBundle\Service\Workflow\CancelStaleWorkflow;
 use Chill\MainBundle\Service\Workflow\CancelStaleWorkflowHandler;
+use Chill\MainBundle\Service\Workflow\CancelStaleWorkflowMessage;
 use Doctrine\Common\Collections\ArrayCollection;
 use Doctrine\ORM\EntityManagerInterface;
 use PHPUnit\Framework\TestCase;
@@ -51,7 +52,7 @@ class CancelStaleWorkflowHandlerTest extends TestCase
 
         $handler = new CancelStaleWorkflowHandler($workflowRepository, $registry, $em, $logger);
 
-        $handler(new CancelStaleWorkflow(1));
+        $handler(new CancelStaleWorkflowMessage(1));
     }
 
     public function testInvokeWorkflowWithMultipleStepsAndValidTransition(): void
@@ -92,7 +93,7 @@ class CancelStaleWorkflowHandlerTest extends TestCase
 
         $handler = new CancelStaleWorkflowHandler($workflowRepository, $registry, $em, $logger);
 
-        $handler(new CancelStaleWorkflow(1));
+        $handler(new CancelStaleWorkflowMessage(1));
     }
 
     public function testInvokeWorkflowWithMultipleStepsAndNoValidTransition(): void
@@ -134,6 +135,6 @@ class CancelStaleWorkflowHandlerTest extends TestCase
 
         $handler = new CancelStaleWorkflowHandler($workflowRepository, $registry, $em, $logger);
 
-        $handler(new CancelStaleWorkflow(1));
+        $handler(new CancelStaleWorkflowMessage(1));
     }
 }