diff --git a/app/Jobs/UpdateSite.php b/app/Jobs/UpdateSite.php
index a278ae8..bff698b 100644
--- a/app/Jobs/UpdateSite.php
+++ b/app/Jobs/UpdateSite.php
@@ -6,7 +6,6 @@
 
 use App\Exceptions\UpdateException;
 use App\Models\Site;
-use App\Models\Update;
 use App\RemoteSite\Connection;
 use App\RemoteSite\Responses\PrepareUpdate;
 use Illuminate\Contracts\Queue\ShouldQueue;
@@ -31,6 +30,14 @@ public function __construct(protected readonly Site $site, protected string $tar
      */
     public function handle(): void
     {
+        $updateCount = $this->site->getUpdateCount($this->targetVersion);
+
+        if ($updateCount >= config('autoupdates.max_update_tries')) {
+            Log::info("Update Loop detected for Site: " . $this->site->id . '; TargetVersion: ' . $this->targetVersion);
+
+            return;
+        }
+
         /** @var Connection $connection */
         $connection = $this->site->connection;
 
diff --git a/app/Models/Site.php b/app/Models/Site.php
index 9df3285..66a4fcf 100644
--- a/app/Models/Site.php
+++ b/app/Models/Site.php
@@ -60,6 +60,11 @@ public function getFrontendStatus(): int
         return $httpClient->get($this->url)->getStatusCode();
     }
 
+    public function getUpdateCount(string $targetVersion): int
+    {
+        return $this->updates()->where('new_version', $targetVersion)->count();
+    }
+
     /**
      * @return HasMany<Update, $this>
      */
diff --git a/config/autoupdates.php b/config/autoupdates.php
index 9f60fd5..0f215b9 100644
--- a/config/autoupdates.php
+++ b/config/autoupdates.php
@@ -4,4 +4,5 @@
     'healthcheck_interval' => env('HEALTH_CHECK_INTERVAL', 24),
     'cleanup_site_delay' => env('CLEANUP_SITE_DELAY', 7),
     'tuf_repo_cachetime' => env('TUF_REPO_CACHETIME', 5),
+    'max_update_tries' => env('MAX_UPDATE_TRIES', 5),
 ];
diff --git a/tests/Unit/Jobs/UpdateSiteTest.php b/tests/Unit/Jobs/UpdateSiteTest.php
index 3e6f283..725a959 100644
--- a/tests/Unit/Jobs/UpdateSiteTest.php
+++ b/tests/Unit/Jobs/UpdateSiteTest.php
@@ -58,6 +58,24 @@ public function testJobQuitsIfNoUpdateIsAvailable()
         $this->assertTrue(true);
     }
 
+    public function testJobQuitsIfWeDetectALoopForAVersion()
+    {
+        $site = $this->getSiteMock([], null, 6);
+
+        Log::spy();
+
+        $object = new UpdateSite($site, "1.0.1");
+        $object->handle();
+
+        Log::shouldHaveReceived('info')
+            ->once()
+            ->withArgs(function ($message) {
+                return str_contains($message, 'Update Loop detected for Site');
+            });
+
+        $this->assertTrue(true);
+    }
+
     public function testJobQuitsIfAvailableUpdateWouldBeAMajorUpdate()
     {
         $site = $this->getSiteMock(
@@ -80,7 +98,6 @@ public function testJobQuitsIfAvailableUpdateWouldBeAMajorUpdate()
 
         $this->assertTrue(true);
     }
-
     public function testJobQuitsIfAvailableUpdateDoesNotMatchTargetVersion()
     {
         $site = $this->getSiteMock(
@@ -167,7 +184,7 @@ public function testJobWritesSuccessLogForSuccessfulJobs()
         $object->handle();
     }
 
-    protected function getSiteMock(array $responses, array $expectedLogRow = null)
+    protected function getSiteMock(array $responses, array $expectedLogRow = null, int $updateCount = 0)
     {
         $connectionMock = $this->getMockBuilder(Connection::class)
             ->disableOriginalConstructor()
@@ -200,12 +217,13 @@ function ($method) use ($responses) {
         }
 
         $siteMock = $this->getMockBuilder(Site::class)
-            ->onlyMethods(['getConnectionAttribute', 'getFrontendStatus', 'updates'])
+            ->onlyMethods(['getConnectionAttribute', 'getFrontendStatus', 'getUpdateCount', 'updates'])
             ->getMock();
 
         $siteMock->method('updates')->willReturn($updateMock);
         $siteMock->method('getConnectionAttribute')->willReturn($connectionMock);
         $siteMock->method('getFrontendStatus')->willReturn(200);
+        $siteMock->method('getUpdateCount')->willReturn($updateCount);
         $siteMock->id = 1;
         $siteMock->url = "http://example.org";
         $siteMock->cms_version = "1.0.0";