diff --git a/psalm.xml b/psalm.xml
index 6906996..08186e8 100644
--- a/psalm.xml
+++ b/psalm.xml
@@ -36,5 +36,10 @@
             </errorLevel>
         </TooManyTemplateParams>
         <PluginIssue name="QueryBuilderSetParameter" errorLevel="suppress"/>
+        <DeprecatedClass>
+            <errorLevel type="suppress">
+                <referencedClass name="Sylius\Bundle\AdminBundle\Menu\OrderShowMenuBuilder"/>
+            </errorLevel>
+        </DeprecatedClass>
     </issueHandlers>
 </psalm>
diff --git a/src/Command/ProcessUploadOrderRequestsCommand.php b/src/Command/ProcessUploadOrderRequestsCommand.php
index f747239..5a732a5 100644
--- a/src/Command/ProcessUploadOrderRequestsCommand.php
+++ b/src/Command/ProcessUploadOrderRequestsCommand.php
@@ -4,6 +4,7 @@
 
 namespace Setono\SyliusPeakPlugin\Command;
 
+use Setono\SyliusPeakPlugin\Processor\FailedUploadOrderRequestProcessorInterface;
 use Setono\SyliusPeakPlugin\Processor\UploadOrderRequestProcessorInterface;
 use Symfony\Component\Console\Attribute\AsCommand;
 use Symfony\Component\Console\Command\Command;
@@ -16,13 +17,17 @@
 )]
 final class ProcessUploadOrderRequestsCommand extends Command
 {
-    public function __construct(private readonly UploadOrderRequestProcessorInterface $uploadOrderRequestProcessor)
-    {
+    public function __construct(
+        private readonly UploadOrderRequestProcessorInterface $uploadOrderRequestProcessor,
+        private readonly FailedUploadOrderRequestProcessorInterface $failedUploadOrderRequestProcessor,
+    ) {
         parent::__construct();
     }
 
     protected function execute(InputInterface $input, OutputInterface $output): int
     {
+        $this->failedUploadOrderRequestProcessor->process();
+
         $this->uploadOrderRequestProcessor->process();
 
         return 0;
diff --git a/src/Event/FailedUploadOrderRequestsQueryBuilderCreatedEvent.php b/src/Event/FailedUploadOrderRequestsQueryBuilderCreatedEvent.php
new file mode 100644
index 0000000..f3696a7
--- /dev/null
+++ b/src/Event/FailedUploadOrderRequestsQueryBuilderCreatedEvent.php
@@ -0,0 +1,18 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\Event;
+
+use Doctrine\ORM\QueryBuilder;
+
+/**
+ * This event is fired when the query builder for failed upload order requests has been created.
+ * Listen to this event if you want to filter on associated orders of the upload order requests.
+ */
+final class FailedUploadOrderRequestsQueryBuilderCreatedEvent
+{
+    public function __construct(public readonly QueryBuilder $queryBuilder)
+    {
+    }
+}
diff --git a/src/EventSubscriber/Workflow/UploadOrderRequest/IncrementTriesSubscriber.php b/src/EventSubscriber/Workflow/UploadOrderRequest/IncrementTriesSubscriber.php
new file mode 100644
index 0000000..e566b88
--- /dev/null
+++ b/src/EventSubscriber/Workflow/UploadOrderRequest/IncrementTriesSubscriber.php
@@ -0,0 +1,28 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest;
+
+use Setono\SyliusPeakPlugin\Model\UploadOrderRequestInterface;
+use Setono\SyliusPeakPlugin\Workflow\UploadOrderRequestWorkflow;
+use Symfony\Component\EventDispatcher\EventSubscriberInterface;
+use Symfony\Component\Workflow\Event\CompletedEvent;
+use Webmozart\Assert\Assert;
+
+final class IncrementTriesSubscriber implements EventSubscriberInterface
+{
+    public static function getSubscribedEvents(): array
+    {
+        return [sprintf('workflow.%s.completed.%s', UploadOrderRequestWorkflow::NAME, UploadOrderRequestWorkflow::TRANSITION_PROCESS) => 'incrementTries'];
+    }
+
+    public function incrementTries(CompletedEvent $event): void
+    {
+        /** @var UploadOrderRequestInterface|object $uploadOrderRequest */
+        $uploadOrderRequest = $event->getSubject();
+        Assert::isInstanceOf($uploadOrderRequest, UploadOrderRequestInterface::class);
+
+        $uploadOrderRequest->incrementTries();
+    }
+}
diff --git a/src/EventSubscriber/Workflow/UploadOrderRequest/RetrySubscriber.php b/src/EventSubscriber/Workflow/UploadOrderRequest/RetrySubscriber.php
new file mode 100644
index 0000000..6808fc5
--- /dev/null
+++ b/src/EventSubscriber/Workflow/UploadOrderRequest/RetrySubscriber.php
@@ -0,0 +1,36 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest;
+
+use Setono\SyliusPeakPlugin\Model\UploadOrderRequestInterface;
+use Setono\SyliusPeakPlugin\Workflow\UploadOrderRequestWorkflow;
+use Symfony\Component\EventDispatcher\EventSubscriberInterface;
+use Symfony\Component\Workflow\Event\CompletedEvent;
+use Webmozart\Assert\Assert;
+
+final class RetrySubscriber implements EventSubscriberInterface
+{
+    public function __construct(private readonly int $maxTries = 5)
+    {
+    }
+
+    public static function getSubscribedEvents(): array
+    {
+        return [sprintf('workflow.%s.completed.%s', UploadOrderRequestWorkflow::NAME, UploadOrderRequestWorkflow::TRANSITION_FAIL) => 'retry'];
+    }
+
+    public function retry(CompletedEvent $event): void
+    {
+        /** @var UploadOrderRequestInterface|object $uploadOrderRequest */
+        $uploadOrderRequest = $event->getSubject();
+        Assert::isInstanceOf($uploadOrderRequest, UploadOrderRequestInterface::class);
+
+        if ($uploadOrderRequest->getTries() >= $this->maxTries) {
+            return;
+        }
+
+        $event->getWorkflow()->apply($uploadOrderRequest, UploadOrderRequestWorkflow::TRANSITION_RESET);
+    }
+}
diff --git a/src/EventSubscriber/Workflow/UploadOrderRequest/StateUpdatedSubscriber.php b/src/EventSubscriber/Workflow/UploadOrderRequest/StateUpdatedSubscriber.php
new file mode 100644
index 0000000..e0382da
--- /dev/null
+++ b/src/EventSubscriber/Workflow/UploadOrderRequest/StateUpdatedSubscriber.php
@@ -0,0 +1,28 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest;
+
+use Setono\SyliusPeakPlugin\Model\UploadOrderRequestInterface;
+use Setono\SyliusPeakPlugin\Workflow\UploadOrderRequestWorkflow;
+use Symfony\Component\EventDispatcher\EventSubscriberInterface;
+use Symfony\Component\Workflow\Event\CompletedEvent;
+use Webmozart\Assert\Assert;
+
+final class StateUpdatedSubscriber implements EventSubscriberInterface
+{
+    public static function getSubscribedEvents(): array
+    {
+        return [sprintf('workflow.%s.completed', UploadOrderRequestWorkflow::NAME) => 'updateTimestamp'];
+    }
+
+    public function updateTimestamp(CompletedEvent $event): void
+    {
+        /** @var UploadOrderRequestInterface|object $uploadOrderRequest */
+        $uploadOrderRequest = $event->getSubject();
+        Assert::isInstanceOf($uploadOrderRequest, UploadOrderRequestInterface::class);
+
+        $uploadOrderRequest->setStateUpdatedAt(new \DateTimeImmutable());
+    }
+}
diff --git a/src/Model/UploadOrderRequest.php b/src/Model/UploadOrderRequest.php
index ca1d47f..85587e4 100644
--- a/src/Model/UploadOrderRequest.php
+++ b/src/Model/UploadOrderRequest.php
@@ -12,6 +12,8 @@ class UploadOrderRequest implements UploadOrderRequestInterface
 
     protected string $state = self::STATE_PENDING;
 
+    protected ?\DateTimeInterface $stateUpdatedAt = null;
+
     protected ?OrderInterface $order = null;
 
     protected ?string $request = null;
@@ -22,6 +24,8 @@ class UploadOrderRequest implements UploadOrderRequestInterface
 
     protected ?int $peakOrderId = null;
 
+    protected int $tries = 0;
+
     public function getId(): ?int
     {
         return $this->id;
@@ -47,6 +51,16 @@ public function setState(string $state): void
         $this->state = $state;
     }
 
+    public function getStateUpdatedAt(): ?\DateTimeInterface
+    {
+        return $this->stateUpdatedAt;
+    }
+
+    public function setStateUpdatedAt(\DateTimeInterface $stateUpdatedAt): void
+    {
+        $this->stateUpdatedAt = $stateUpdatedAt;
+    }
+
     public function getOrder(): ?OrderInterface
     {
         return $this->order;
@@ -96,4 +110,19 @@ public function setPeakOrderId(?int $peakOrderId): void
     {
         $this->peakOrderId = $peakOrderId;
     }
+
+    public function getTries(): int
+    {
+        return $this->tries;
+    }
+
+    public function setTries(int $tries): void
+    {
+        $this->tries = $tries;
+    }
+
+    public function incrementTries(): void
+    {
+        ++$this->tries;
+    }
 }
diff --git a/src/Model/UploadOrderRequestInterface.php b/src/Model/UploadOrderRequestInterface.php
index 70a3adb..d949e6c 100644
--- a/src/Model/UploadOrderRequestInterface.php
+++ b/src/Model/UploadOrderRequestInterface.php
@@ -23,6 +23,10 @@ public function getState(): string;
 
     public function setState(string $state): void;
 
+    public function getStateUpdatedAt(): ?\DateTimeInterface;
+
+    public function setStateUpdatedAt(\DateTimeInterface $stateUpdatedAt): void;
+
     public function getOrder(): ?OrderInterface;
 
     public function setOrder(?OrderInterface $order): void;
@@ -45,4 +49,10 @@ public function setError(?string $error): void;
     public function getPeakOrderId(): ?int;
 
     public function setPeakOrderId(?int $peakOrderId): void;
+
+    public function getTries(): int;
+
+    public function setTries(int $tries): void;
+
+    public function incrementTries(): void;
 }
diff --git a/src/Processor/FailedUploadOrderRequestProcessor.php b/src/Processor/FailedUploadOrderRequestProcessor.php
new file mode 100644
index 0000000..2f0cec1
--- /dev/null
+++ b/src/Processor/FailedUploadOrderRequestProcessor.php
@@ -0,0 +1,43 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\Processor;
+
+use Doctrine\ORM\OptimisticLockException;
+use Doctrine\Persistence\ManagerRegistry;
+use Setono\Doctrine\ORMTrait;
+use Setono\SyliusPeakPlugin\Provider\FailedUploadOrderRequestsProviderInterface;
+use Setono\SyliusPeakPlugin\Workflow\UploadOrderRequestWorkflow;
+use Symfony\Component\Workflow\Exception\LogicException;
+use Symfony\Component\Workflow\WorkflowInterface;
+
+final class FailedUploadOrderRequestProcessor implements FailedUploadOrderRequestProcessorInterface
+{
+    use ORMTrait;
+
+    public function __construct(
+        private readonly FailedUploadOrderRequestsProviderInterface $failedUploadOrderRequestsProvider,
+        private readonly WorkflowInterface $uploadOrderRequestWorkflow,
+        ManagerRegistry $managerRegistry,
+    ) {
+        $this->managerRegistry = $managerRegistry;
+    }
+
+    public function process(): void
+    {
+        foreach ($this->failedUploadOrderRequestsProvider->getUploadOrderRequests() as $uploadOrderRequest) {
+            try {
+                $this->uploadOrderRequestWorkflow->apply($uploadOrderRequest, UploadOrderRequestWorkflow::TRANSITION_FAIL);
+            } catch (LogicException) {
+                continue;
+            }
+
+            try {
+                $this->getManager($uploadOrderRequest)->flush();
+            } catch (OptimisticLockException) {
+                continue;
+            }
+        }
+    }
+}
diff --git a/src/Processor/FailedUploadOrderRequestProcessorInterface.php b/src/Processor/FailedUploadOrderRequestProcessorInterface.php
new file mode 100644
index 0000000..e46b08d
--- /dev/null
+++ b/src/Processor/FailedUploadOrderRequestProcessorInterface.php
@@ -0,0 +1,10 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\Processor;
+
+interface FailedUploadOrderRequestProcessorInterface
+{
+    public function process(): void;
+}
diff --git a/src/Processor/UploadOrderRequestProcessor.php b/src/Processor/UploadOrderRequestProcessor.php
index 6f68899..dbcd4cd 100644
--- a/src/Processor/UploadOrderRequestProcessor.php
+++ b/src/Processor/UploadOrderRequestProcessor.php
@@ -19,7 +19,7 @@ final class UploadOrderRequestProcessor implements UploadOrderRequestProcessorIn
     use ORMTrait;
 
     public function __construct(
-        private readonly PreQualifiedUploadOrderRequestsProviderInterface $preQualifiedUploadableOrdersProvider,
+        private readonly PreQualifiedUploadOrderRequestsProviderInterface $preQualifiedUploadOrderRequestsProvider,
         private readonly MessageBusInterface $commandBus,
         private readonly WorkflowInterface $uploadOrderRequestWorkflow,
         ManagerRegistry $managerRegistry,
@@ -29,7 +29,7 @@ public function __construct(
 
     public function process(): void
     {
-        foreach ($this->preQualifiedUploadableOrdersProvider->getUploadOrderRequests() as $uploadOrderRequest) {
+        foreach ($this->preQualifiedUploadOrderRequestsProvider->getUploadOrderRequests() as $uploadOrderRequest) {
             try {
                 $this->uploadOrderRequestWorkflow->apply($uploadOrderRequest, UploadOrderRequestWorkflow::TRANSITION_PROCESS);
             } catch (LogicException) {
diff --git a/src/Provider/FailedUploadOrderRequestsProvider.php b/src/Provider/FailedUploadOrderRequestsProvider.php
new file mode 100644
index 0000000..5153a5f
--- /dev/null
+++ b/src/Provider/FailedUploadOrderRequestsProvider.php
@@ -0,0 +1,49 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\Provider;
+
+use Doctrine\Persistence\ManagerRegistry;
+use DoctrineBatchUtils\BatchProcessing\SelectBatchIteratorAggregate;
+use Psr\EventDispatcher\EventDispatcherInterface;
+use Setono\Doctrine\ORMTrait;
+use Setono\SyliusPeakPlugin\Event\FailedUploadOrderRequestsQueryBuilderCreatedEvent;
+use Setono\SyliusPeakPlugin\Model\UploadOrderRequestInterface;
+
+final class FailedUploadOrderRequestsProvider implements FailedUploadOrderRequestsProviderInterface
+{
+    use ORMTrait;
+
+    /**
+     * @param class-string<UploadOrderRequestInterface> $uploadOrderRequestClass
+     */
+    public function __construct(
+        ManagerRegistry $managerRegistry,
+        private readonly EventDispatcherInterface $eventDispatcher,
+        private readonly string $uploadOrderRequestClass,
+        private readonly string $processingTimeout = '1 hour',
+    ) {
+        $this->managerRegistry = $managerRegistry;
+    }
+
+    /**
+     * @return \Generator<array-key, UploadOrderRequestInterface>
+     */
+    public function getUploadOrderRequests(): \Generator
+    {
+        $qb = $this->getRepository($this->uploadOrderRequestClass)->createQueryBuilder('o')
+            ->andWhere('o.state = :orderState')
+            ->andWhere('o.stateUpdatedAt < :stateUpdatedAt')
+            ->setParameter('state', UploadOrderRequestInterface::STATE_PROCESSING)
+            ->setParameter('stateUpdatedAt', new \DateTimeImmutable('-' . $this->processingTimeout))
+        ;
+
+        $this->eventDispatcher->dispatch(new FailedUploadOrderRequestsQueryBuilderCreatedEvent($qb));
+
+        /** @var SelectBatchIteratorAggregate<array-key, UploadOrderRequestInterface> $iterator */
+        $iterator = SelectBatchIteratorAggregate::fromQuery($qb->getQuery(), 50);
+
+        yield from $iterator;
+    }
+}
diff --git a/src/Provider/FailedUploadOrderRequestsProviderInterface.php b/src/Provider/FailedUploadOrderRequestsProviderInterface.php
new file mode 100644
index 0000000..d22980d
--- /dev/null
+++ b/src/Provider/FailedUploadOrderRequestsProviderInterface.php
@@ -0,0 +1,15 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Setono\SyliusPeakPlugin\Provider;
+
+use Setono\SyliusPeakPlugin\Model\UploadOrderRequestInterface;
+
+interface FailedUploadOrderRequestsProviderInterface
+{
+    /**
+     * @return iterable<array-key, UploadOrderRequestInterface>
+     */
+    public function getUploadOrderRequests(): iterable;
+}
diff --git a/src/Resources/config/doctrine/model/UploadOrderRequest.orm.xml b/src/Resources/config/doctrine/model/UploadOrderRequest.orm.xml
index 9ec4fc1..55ce0ca 100644
--- a/src/Resources/config/doctrine/model/UploadOrderRequest.orm.xml
+++ b/src/Resources/config/doctrine/model/UploadOrderRequest.orm.xml
@@ -11,14 +11,20 @@
         </id>
 
         <field name="version" type="integer" version="true"/>
-        <field name="state" type="string"/>
+        <field name="state" column="state" type="string"/>
+        <field name="stateUpdatedAt" column="state_updated_at" type="datetime" nullable="true"/>
         <field name="request" type="text" nullable="true"/>
         <field name="response" type="text" nullable="true"/>
         <field name="error" type="text" nullable="true"/>
         <field name="peakOrderId" type="integer" nullable="true"/>
+        <field name="tries" type="integer"/>
 
         <one-to-one field="order" target-entity="Sylius\Component\Order\Model\OrderInterface" inversed-by="peakUploadOrderRequest">
             <join-column name="order_id" referenced-column-name="id" nullable="false" unique="true" on-delete="CASCADE"/>
         </one-to-one>
+
+        <indexes>
+            <index columns="state,state_updated_at"/>
+        </indexes>
     </mapped-superclass>
 </doctrine-mapping>
diff --git a/src/Resources/config/services/command.xml b/src/Resources/config/services/command.xml
index 8a4af7d..6ad8df3 100644
--- a/src/Resources/config/services/command.xml
+++ b/src/Resources/config/services/command.xml
@@ -12,6 +12,7 @@
 
         <service id="Setono\SyliusPeakPlugin\Command\ProcessUploadOrderRequestsCommand">
             <argument type="service" id="Setono\SyliusPeakPlugin\Processor\UploadOrderRequestProcessorInterface"/>
+            <argument type="service" id="Setono\SyliusPeakPlugin\Processor\FailedUploadOrderRequestProcessorInterface"/>
 
             <tag name="console.command"/>
         </service>
diff --git a/src/Resources/config/services/event_subscriber.xml b/src/Resources/config/services/event_subscriber.xml
index ff70bcf..3d5a546 100644
--- a/src/Resources/config/services/event_subscriber.xml
+++ b/src/Resources/config/services/event_subscriber.xml
@@ -48,6 +48,19 @@
             <tag name="kernel.event_subscriber"/>
         </service>
 
+        <!-- Workflow: Upload Order Request -->
+        <service id="Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest\IncrementTriesSubscriber">
+            <tag name="kernel.event_subscriber"/>
+        </service>
+
+        <service id="Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest\RetrySubscriber">
+            <tag name="kernel.event_subscriber"/>
+        </service>
+
+        <service id="Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadOrderRequest\StateUpdatedSubscriber">
+            <tag name="kernel.event_subscriber"/>
+        </service>
+
         <!-- Workflow: Upload Product Variant Request -->
         <service id="Setono\SyliusPeakPlugin\EventSubscriber\Workflow\UploadProductVariantRequest\ResetSubscriber">
             <tag name="kernel.event_subscriber"/>
diff --git a/src/Resources/config/services/processor.xml b/src/Resources/config/services/processor.xml
index 5486295..02fc86d 100644
--- a/src/Resources/config/services/processor.xml
+++ b/src/Resources/config/services/processor.xml
@@ -2,6 +2,15 @@
 <container xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://symfony.com/schema/dic/services"
            xsi:schemaLocation="http://symfony.com/schema/dic/services http://symfony.com/schema/dic/services/services-1.0.xsd">
     <services>
+        <service id="Setono\SyliusPeakPlugin\Processor\FailedUploadOrderRequestProcessorInterface"
+                 alias="Setono\SyliusPeakPlugin\Processor\FailedUploadOrderRequestProcessor"/>
+
+        <service id="Setono\SyliusPeakPlugin\Processor\FailedUploadOrderRequestProcessor">
+            <argument type="service" id="Setono\SyliusPeakPlugin\Provider\FailedUploadOrderRequestsProviderInterface"/>
+            <argument type="service" id="state_machine.setono_sylius_peak__upload_order_request"/>
+            <argument type="service" id="doctrine"/>
+        </service>
+
         <service id="Setono\SyliusPeakPlugin\Processor\UploadOrderRequestProcessorInterface"
                  alias="Setono\SyliusPeakPlugin\Processor\UploadOrderRequestProcessor"/>
 
diff --git a/src/Resources/config/services/provider.xml b/src/Resources/config/services/provider.xml
index e23625d..08db1c5 100644
--- a/src/Resources/config/services/provider.xml
+++ b/src/Resources/config/services/provider.xml
@@ -2,6 +2,15 @@
 <container xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://symfony.com/schema/dic/services"
            xsi:schemaLocation="http://symfony.com/schema/dic/services http://symfony.com/schema/dic/services/services-1.0.xsd">
     <services>
+        <service id="Setono\SyliusPeakPlugin\Provider\FailedUploadOrderRequestsProviderInterface"
+                 alias="Setono\SyliusPeakPlugin\Provider\FailedUploadOrderRequestsProvider"/>
+
+        <service id="Setono\SyliusPeakPlugin\Provider\FailedUploadOrderRequestsProvider">
+            <argument type="service" id="doctrine"/>
+            <argument type="service" id="event_dispatcher"/>
+            <argument>%setono_sylius_peak.model.upload_order_request.class%</argument>
+        </service>
+
         <service id="Setono\SyliusPeakPlugin\Provider\PreQualifiedUploadOrderRequestsProviderInterface"
                  alias="Setono\SyliusPeakPlugin\Provider\PreQualifiedUploadOrderRequestsProvider"/>