diff --git a/app/Modules/Platform/Http/Controllers/SchedulerMonitoringController.php b/app/Modules/Platform/Http/Controllers/SchedulerMonitoringController.php
index 8efb786b..6c8210d4 100644
--- a/app/Modules/Platform/Http/Controllers/SchedulerMonitoringController.php
+++ b/app/Modules/Platform/Http/Controllers/SchedulerMonitoringController.php
@@ -6,6 +6,9 @@ namespace App\Modules\Platform\Http\Controllers;
 
 use App\Http\Controllers\Controller;
 use App\Modules\Platform\Scheduling\ScheduledTaskRun;
+use App\Modules\Platform\Settings\Setting;
+use App\Modules\Platform\Settings\Settings;
+use App\Modules\Platform\Updates\LatestReleaseInfo;
 use App\Support\Pagination;
 use Illuminate\Http\RedirectResponse;
 use Illuminate\Http\Request;
@@ -48,13 +51,16 @@ class SchedulerMonitoringController extends Controller
 
     public function __construct(
         private readonly FailedJobProviderInterface $failer,
+        private readonly LatestReleaseInfo $latestRelease,
+        private readonly Settings $settings,
     ) {}
 
     public function index(Request $request): Response|RedirectResponse
     {
         $runs = ScheduledTaskRun::query()->get()->keyBy('command');
+        $details = $this->details();
 
-        $tasks = collect(self::KNOWN_COMMANDS)->map(function (string $label, string $command) use ($runs): array {
+        $tasks = collect(self::KNOWN_COMMANDS)->map(function (string $label, string $command) use ($runs, $details): array {
             $run = $runs->get($command);
 
             return [
@@ -62,6 +68,7 @@ class SchedulerMonitoringController extends Controller
                 'label' => $label,
                 'status' => $run?->status->value,
                 'message' => $run?->message,
+                'detail' => $details[$command] ?? null,
                 'duration_ms' => $run?->duration_ms,
                 'ran_at' => $run?->ran_at?->toIso8601String(),
             ];
@@ -137,4 +144,32 @@ class SchedulerMonitoringController extends Controller
 
         return back()->with('success', __('All failed jobs deleted.'));
     }
+
+    /**
+     * What a task actually found, for the tasks that find something.
+     *
+     * The run rows answer "did it work"; they cannot answer "and what did
+     * it say", because Laravel's ScheduledTaskFinished event fires after
+     * the command returns and carries no output — which is why a
+     * successful check for updates has always shown an empty Message.
+     * Joined here at render time instead, from what the command itself
+     * wrote to the settings, so the line stays true whether the daily job
+     * or somebody pressing the button did the work.
+     *
+     * @return array<string, string>
+     */
+    private function details(): array
+    {
+        $release = $this->latestRelease->current();
+        $checkedAt = $this->settings->get(Setting::LatestVersionCheckedAt);
+        $everChecked = is_string($checkedAt) && $checkedAt !== '';
+
+        $updates = match (true) {
+            $release !== null => (string) __(':version is available', ['version' => $release['version']]),
+            $everChecked => (string) __('Up to date'),
+            default => null,
+        };
+
+        return array_filter(['projectsend:check-for-updates' => $updates]);
+    }
 }
diff --git a/resources/js/pages/system/settings/scheduler.tsx b/resources/js/pages/system/settings/scheduler.tsx
index 5088d762..84e82d7c 100644
--- a/resources/js/pages/system/settings/scheduler.tsx
+++ b/resources/js/pages/system/settings/scheduler.tsx
@@ -16,6 +16,8 @@ interface ScheduledTask {
     label: string;
     status: 'success' | 'failed' | null;
     message: string | null;
+    /** What the task found, for the tasks that find something. Never set on a failure. */
+    detail: string | null;
     duration_ms: number | null;
     ran_at: string | null;
 }
@@ -130,7 +132,10 @@ export default function SchedulerSettings({
                                         <td className="text-muted-foreground px-4 py-2.5 whitespace-nowrap">
                                             {task.duration_ms !== null ? `${task.duration_ms} ms` : '—'}
                                         </td>
-                                        <td className="text-muted-foreground max-w-xs px-4 py-2.5 break-words">{task.message ?? '—'}</td>
+                                        {/* A failure's own message wins: what the
+                                            last successful run found is not the
+                                            answer to why this one broke. */}
+                                        <td className="text-muted-foreground max-w-xs px-4 py-2.5 break-words">{task.message ?? task.detail ?? '—'}</td>
                                     </tr>
                                 ))}
                             </tbody>
diff --git a/tests/Feature/Platform/SchedulerMonitoringTest.php b/tests/Feature/Platform/SchedulerMonitoringTest.php
index d951c4a7..e5d680b0 100644
--- a/tests/Feature/Platform/SchedulerMonitoringTest.php
+++ b/tests/Feature/Platform/SchedulerMonitoringTest.php
@@ -7,6 +7,8 @@ use App\Modules\Identity\Models\Role;
 use App\Modules\Platform\Capabilities\Edition;
 use App\Modules\Platform\Scheduling\ScheduledTaskRun;
 use App\Modules\Platform\Scheduling\TaskRunStatus;
+use App\Modules\Platform\Settings\Setting;
+use App\Modules\Platform\Settings\Settings;
 use Illuminate\Support\Facades\DB;
 use Illuminate\Support\Str;
 use Illuminate\Testing\TestResponse;
@@ -167,3 +169,38 @@ test('staff without edit_settings cannot access the scheduler page', function ()
 
     $this->actingAs($staffer)->get('/system/settings/scheduler')->assertForbidden();
 });
+
+test('the update check reports what it found, not just that it ran', function () {
+    config()->set('projectsend.version', '2.0.0');
+    $settings = app(Settings::class);
+    $settings->set(Setting::LatestVersionCheckedAt, now()->toIso8601String());
+    $settings->set(Setting::LatestKnownVersion, '2.5.0');
+
+    $response = $this->actingAs($this->admin)->get('/system/settings/scheduler');
+    $tasks = collect(schedulerPageProps($response)['tasks'])->keyBy('command');
+
+    expect($tasks->get('projectsend:check-for-updates')['detail'])->toContain('2.5.0');
+});
+
+test('a check that found nothing newer says so', function () {
+    config()->set('projectsend.version', '2.0.0');
+    $settings = app(Settings::class);
+    $settings->set(Setting::LatestVersionCheckedAt, now()->toIso8601String());
+    $settings->set(Setting::LatestKnownVersion, '2.0.0');
+
+    $response = $this->actingAs($this->admin)->get('/system/settings/scheduler');
+    $tasks = collect(schedulerPageProps($response)['tasks'])->keyBy('command');
+
+    expect($tasks->get('projectsend:check-for-updates')['detail'])->toBe('Up to date');
+});
+
+test('a check that has never run has nothing to report', function () {
+    $settings = app(Settings::class);
+    $settings->set(Setting::LatestVersionCheckedAt, '');
+    $settings->set(Setting::LatestKnownVersion, '');
+
+    $response = $this->actingAs($this->admin)->get('/system/settings/scheduler');
+    $tasks = collect(schedulerPageProps($response)['tasks'])->keyBy('command');
+
+    expect($tasks->get('projectsend:check-for-updates')['detail'])->toBeNull();
+});