diff --git a/app/Jobs/ApiTokenExpirationWarningJob.php b/app/Jobs/ApiTokenExpirationWarningJob.php
index 810919c6a..e7b34248e 100644
--- a/app/Jobs/ApiTokenExpirationWarningJob.php
+++ b/app/Jobs/ApiTokenExpirationWarningJob.php
@@ -42,6 +42,9 @@ public function handle(): void
                     }
 
                     $warningSentAt = now();
+
+                    $team->notify(new ApiTokenExpiringNotification($token));
+
                     $markedAsSent = PersonalAccessToken::query()
                         ->whereKey($token->getKey())
                         ->whereNotNull('expires_at')
@@ -55,7 +58,6 @@ public function handle(): void
                     }
 
                     $token->forceFill(['api_token_expiration_warning_sent_at' => $warningSentAt]);
-                    $team->notify(new ApiTokenExpiringNotification($token));
                 }
             });
     }
diff --git a/tests/Feature/ApiTokenExpirationWarningTest.php b/tests/Feature/ApiTokenExpirationWarningTest.php
index 67380f047..beea1f126 100644
--- a/tests/Feature/ApiTokenExpirationWarningTest.php
+++ b/tests/Feature/ApiTokenExpirationWarningTest.php
@@ -6,6 +6,7 @@
 use App\Models\User;
 use App\Notifications\ApiTokenExpiringNotification;
 use Carbon\Carbon;
+use Illuminate\Contracts\Notifications\Dispatcher;
 use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Facades\Cache;
 use Illuminate\Support\Facades\Notification;
@@ -50,6 +51,21 @@ function createTokenExpiring(User $user, Team $team, ?Carbon $expiresAt, ?Carbon
         expect($token->fresh()->api_token_expiration_warning_sent_at)->not->toBeNull();
     });
 
+    test('does not mark token as warned when notification fails', function () {
+        $token = createTokenExpiring($this->user, $this->team, now()->addHours(23));
+        $dispatcher = Mockery::mock(Dispatcher::class);
+        $dispatcher->shouldReceive('send')
+            ->once()
+            ->andThrow(new RuntimeException('Notification failed'));
+
+        $this->app->instance(Dispatcher::class, $dispatcher);
+
+        expect(fn () => (new ApiTokenExpirationWarningJob)->handle())
+            ->toThrow(RuntimeException::class, 'Notification failed');
+
+        expect($token->fresh()->api_token_expiration_warning_sent_at)->toBeNull();
+    });
+
     test('database marker prevents duplicate warnings on repeat runs', function () {
         createTokenExpiring($this->user, $this->team, now()->addHours(12));