diff --git a/.ai/lessons.md b/.ai/lessons.md
index d9365ef354..1ea84dab0f 100644
--- a/.ai/lessons.md
+++ b/.ai/lessons.md
@@ -26,6 +26,7 @@
 - Do not symlink `vendor` into another worktree. Composer resolves the base path from the real `vendor` path, so the tests load the app classes of the other checkout. Run `composer install --ignore-platform-req=ext-zip` in the worktree.
 - To assert that the unsaved-changes bar shows, check `el.classList.contains('is-dirty')`. Playwright treats the hidden bar (`opacity-0`) as visible, and its class attribute always contains the text `is-dirty` from Tailwind variants.
 - Do not call `sleep()` in a browser test. The app server runs in the test process, so `sleep()` stops it; use `$page->wait()`.
+- `Queue::fake()` also captures `dispatchSync()` of a `ShouldQueue` job, so the job never runs. Fake only the jobs to block (`Queue::fake([SomeJob::class])`).
 - In tests, turning on `is_metrics_enabled` (and other Sentinel settings) with `save()`/`update()` runs the settings hook, which starts Sentinel over a real SSH connection on the sync queue. Use `saveQuietly()` or `Queue::fake()`.
 - Call `visit()` directly in each `tests/v4/Browser` test body; Pest does not mark a test that only uses helper-wrapped `visit()` as a browser test, so it fails with `sendText() on null`.
 - SQLite returns `0`/`1` for boolean columns without a `boolean` cast, while Postgres returns real booleans. A strict `=== false` check on such a column never matches in tests, so tests can pass on behavior that Postgres blocks. Add the cast or compare loosely.
diff --git a/app/Jobs/CheckForUpdatesJob.php b/app/Jobs/CheckForUpdatesJob.php
index 2c16b4475e..2414238b86 100644
--- a/app/Jobs/CheckForUpdatesJob.php
+++ b/app/Jobs/CheckForUpdatesJob.php
@@ -8,6 +8,7 @@ use Illuminate\Contracts\Queue\ShouldQueue;
 use Illuminate\Foundation\Bus\Dispatchable;
 use Illuminate\Queue\InteractsWithQueue;
 use Illuminate\Queue\SerializesModels;
+use Illuminate\Support\Facades\Log;
 
 class CheckForUpdatesJob implements ShouldBeEncrypted, ShouldQueue
 {
@@ -21,15 +22,18 @@ class CheckForUpdatesJob implements ShouldBeEncrypted, ShouldQueue
         $this->cdnTries = $cdnTries;
     }
 
-    public function handle(): void
+    /**
+     * @return bool Whether the check finished and new_version_available is up to date
+     */
+    public function handle(): bool
     {
         try {
             if (isDev() || isCloud()) {
-                return;
+                return false;
             }
             $versions = refresh_versions_file($this->cdnTries);
             if ($versions === null) {
-                return;
+                return false;
             }
 
             CheckTraefikVersionJob::dispatch();
@@ -37,8 +41,12 @@ class CheckForUpdatesJob implements ShouldBeEncrypted, ShouldQueue
             $latestVersion = data_get($versions, 'coolify.v4.version');
             $newVersionAvailable = version_compare($latestVersion, config('constants.coolify.version'), '>');
             instanceSettings()->update(['new_version_available' => $newVersionAvailable]);
+
+            return true;
         } catch (\Throwable $e) {
-            // Consider implementing a notification to administrators
+            Log::warning('Could not check for Coolify updates', ['error' => $e->getMessage()]);
+
+            return false;
         }
     }
 }
diff --git a/app/Livewire/Settings/Updates.php b/app/Livewire/Settings/Updates.php
index 27fe705423..8fd02e046e 100644
--- a/app/Livewire/Settings/Updates.php
+++ b/app/Livewire/Settings/Updates.php
@@ -159,10 +159,14 @@ class Updates extends Component
     public function checkManually()
     {
         $this->authorize('update', $this->settings);
-        CheckForUpdatesJob::dispatchSync(cdnTries: 1);
+        $checked = (new CheckForUpdatesJob(cdnTries: 1))->handle();
         $this->dispatch('updateAvailable');
-        $settings = instanceSettings();
-        if ($settings->new_version_available) {
+        if (! $checked) {
+            $this->dispatch('error', 'Could not check for updates. Try again later.');
+
+            return;
+        }
+        if (instanceSettings()->new_version_available) {
             $this->dispatch('success', 'New version available!');
         } else {
             $this->dispatch('success', 'No new version available.');
diff --git a/tests/Feature/SettingsUpdatesCheckNowTest.php b/tests/Feature/SettingsUpdatesCheckNowTest.php
new file mode 100644
index 0000000000..dbdd049fd9
--- /dev/null
+++ b/tests/Feature/SettingsUpdatesCheckNowTest.php
@@ -0,0 +1,52 @@
+<?php
+
+use App\Jobs\CheckTraefikVersionJob;
+use App\Livewire\Settings\Updates;
+use App\Models\InstanceSettings;
+use App\Models\Server;
+use App\Models\Team;
+use App\Models\User;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\File;
+use Illuminate\Support\Facades\Http;
+use Illuminate\Support\Facades\Queue;
+use Illuminate\Support\Once;
+use Livewire\Livewire;
+
+uses(RefreshDatabase::class);
+
+beforeEach(function () {
+    Queue::fake([CheckTraefikVersionJob::class]);
+    config()->set('constants.coolify.version', '4.4.6');
+
+    $rootTeam = Team::find(0) ?? Team::factory()->create(['id' => 0]);
+    Server::factory()->create(['id' => 0, 'team_id' => $rootTeam->id]);
+    InstanceSettings::forceCreate(['id' => 0]);
+    Once::flush();
+
+    $user = User::factory()->create();
+    $rootTeam->members()->attach($user->id, ['role' => 'admin']);
+    $this->actingAs($user);
+    session(['currentTeam' => ['id' => $rootTeam->id]]);
+});
+
+it('reports a failed CDN request instead of "No new version available"', function () {
+    Http::fake(['*' => Http::response('error code: 1200', 503)]);
+    File::partialMock()->shouldReceive('put')->with(base_path('versions.json'), Mockery::any())->never();
+
+    Livewire::test(Updates::class)
+        ->call('checkManually')
+        ->assertDispatched('error', 'Could not check for updates. Try again later.')
+        ->assertNotDispatched('success');
+});
+
+it('reports a new version when the CDN has a newer version', function () {
+    Http::fake(['*' => Http::response(['coolify' => ['v4' => ['version' => '4.4.7']]])]);
+    File::partialMock()->shouldReceive('put')->with(base_path('versions.json'), Mockery::any())->once();
+
+    Livewire::test(Updates::class)
+        ->call('checkManually')
+        ->assertDispatched('success', 'New version available!');
+
+    expect(InstanceSettings::get()->new_version_available)->toBeTruthy();
+});