diff --git a/app/Exceptions/Handler.php b/app/Exceptions/Handler.php
index c9cbeab..ec1146a 100644
--- a/app/Exceptions/Handler.php
+++ b/app/Exceptions/Handler.php
@@ -3,6 +3,7 @@
 namespace App\Exceptions;
 
 use App\Support\ApiError;
+use App\Support\SentryReporter;
 use Illuminate\Database\Connectors\ConnectionException as DatabaseConnectionException;
 use Illuminate\Database\QueryException;
 use Illuminate\Foundation\Exceptions\Handler as ExceptionHandler;
@@ -43,13 +44,9 @@ class Handler extends ExceptionHandler
                 return;
             }
 
-            if (! app()->bound('sentry') || empty(config('sentry.dsn'))) {
-                return;
-            }
-
             $this->configureSentryScope();
 
-            app('sentry')->captureException($e);
+            SentryReporter::captureException($e);
         });
     }
 
diff --git a/app/Http/Controllers/Api/Tenant/OnboardingController.php b/app/Http/Controllers/Api/Tenant/OnboardingController.php
index 54b36ba..41e0703 100644
--- a/app/Http/Controllers/Api/Tenant/OnboardingController.php
+++ b/app/Http/Controllers/Api/Tenant/OnboardingController.php
@@ -34,6 +34,8 @@ class OnboardingController extends Controller
                 'admin_app_opened_at' => Arr::get($settings, 'onboarding.admin_app_opened_at'),
                 'primary_event_id' => Arr::get($settings, 'onboarding.primary_event_id'),
                 'selected_packages' => Arr::get($settings, 'onboarding.selected_packages'),
+                'dismissed_at' => Arr::get($settings, 'onboarding.dismissed_at'),
+                'completed_at' => Arr::get($settings, 'onboarding.completed_at'),
                 'branding_completed' => (bool) ($status['palette'] ?? false),
                 'tasks_configured' => (bool) ($status['packages'] ?? false),
                 'event_created' => (bool) ($status['event'] ?? false),
@@ -84,6 +86,10 @@ class OnboardingController extends Controller
                 Arr::set($settings, 'onboarding.invite_created_at', Carbon::now()->toIso8601String());
                 break;
 
+            case 'dismissed':
+                Arr::set($settings, 'onboarding.dismissed_at', Carbon::now()->toIso8601String());
+                break;
+
             case 'completed':
                 TenantOnboardingState::markCompleted($tenant, $meta);
                 break;
diff --git a/app/Providers/AppServiceProvider.php b/app/Providers/AppServiceProvider.php
index da8bb05..473845d 100644
--- a/app/Providers/AppServiceProvider.php
+++ b/app/Providers/AppServiceProvider.php
@@ -32,8 +32,10 @@ use App\Services\Checkout\CheckoutSessionService;
 use App\Services\Security\PhotoSecurityScanner;
 use App\Services\Storage\EventStorageManager;
 use App\Services\Storage\StorageHealthService;
+use App\Support\SentryReporter;
 use App\Testing\Mailbox;
 use Illuminate\Cache\RateLimiting\Limit;
+use Illuminate\Console\Events\ScheduledTaskFailed;
 use Illuminate\Http\Request;
 use Illuminate\Mail\Events\MessageSent;
 use Illuminate\Queue\Events\JobFailed;
@@ -241,36 +243,63 @@ class AppServiceProvider extends ServiceProvider
             ];
         });
 
-        if (config('storage-monitor.queue_failure_alerts')) {
-            Queue::failing(function (JobFailed $event) {
-                $context = [
-                    'queue' => $event->job->getQueue(),
-                    'job' => $event->job->resolveName(),
-                    'exception' => $event->exception->getMessage(),
-                ];
+        Queue::failing(function (JobFailed $event) {
+            $context = [
+                'queue' => $event->job->getQueue(),
+                'job' => $event->job->resolveName(),
+                'exception' => $event->exception->getMessage(),
+            ];
 
-                $command = data_get($event->job->payload(), 'data.command');
+            $command = data_get($event->job->payload(), 'data.command');
 
-                if (is_string($command)) {
-                    try {
-                        $instance = @unserialize($command, ['allowed_classes' => true]);
-                        if (is_object($instance)) {
-                            foreach (['eventId' => 'event_id', 'photoId' => 'photo_id'] as $property => $label) {
-                                if (isset($instance->{$property})) {
-                                    $context[$label] = $instance->{$property};
-                                }
+            if (is_string($command)) {
+                try {
+                    $instance = @unserialize($command, ['allowed_classes' => true]);
+                    if (is_object($instance)) {
+                        foreach (['eventId' => 'event_id', 'photoId' => 'photo_id'] as $property => $label) {
+                            if (isset($instance->{$property})) {
+                                $context[$label] = $instance->{$property};
                             }
                         }
-                    } catch (\Throwable $e) {
-                        $context['unserialize_error'] = $e->getMessage();
                     }
+                } catch (\Throwable $e) {
+                    $context['unserialize_error'] = $e->getMessage();
                 }
+            }
 
+            SentryReporter::captureException($event->exception, [
+                'tags' => [
+                    'queue' => $context['queue'],
+                    'job' => $context['job'],
+                    'connection' => $event->connectionName,
+                ],
+                'extra' => [
+                    'event_id' => $context['event_id'] ?? null,
+                    'photo_id' => $context['photo_id'] ?? null,
+                ],
+            ]);
+
+            if (config('storage-monitor.queue_failure_alerts')) {
                 if ($mail = config('storage-monitor.alert_recipients.mail')) {
                     Notification::route('mail', $mail)->notify(new UploadPipelineFailed($context));
                 }
-            });
-        }
+            }
+        });
+
+        EventFacade::listen(ScheduledTaskFailed::class, function (ScheduledTaskFailed $event): void {
+            $task = $event->task;
+
+            SentryReporter::captureException($event->exception, [
+                'tags' => [
+                    'schedule_command' => $task->command ?? 'unknown',
+                    'schedule_expression' => $task->expression ?? null,
+                ],
+                'extra' => [
+                    'schedule_description' => $task->description ?? null,
+                    'schedule_timezone' => $task->timezone ?? null,
+                ],
+            ]);
+        });
 
         if ($this->app->runningInConsole()) {
             $this->app->register(\App\Providers\Filament\AdminPanelProvider::class);
diff --git a/app/Services/Addons/EventAddonCheckoutService.php b/app/Services/Addons/EventAddonCheckoutService.php
index 0d6dc80..ce4084d 100644
--- a/app/Services/Addons/EventAddonCheckoutService.php
+++ b/app/Services/Addons/EventAddonCheckoutService.php
@@ -5,8 +5,8 @@ namespace App\Services\Addons;
 use App\Models\Event;
 use App\Models\EventPackageAddon;
 use App\Models\Tenant;
-use App\Services\Paddle\PaddleCustomerService;
 use App\Services\Paddle\PaddleClient;
+use App\Services\Paddle\PaddleCustomerService;
 use Illuminate\Support\Arr;
 use Illuminate\Support\Facades\Log;
 use Illuminate\Support\Str;
@@ -86,15 +86,20 @@ class EventAddonCheckoutService
                     'quantity' => $quantity,
                 ],
             ],
-            'metadata' => $metadata,
-            'success_url' => $payload['success_url'] ?? null,
-            'cancel_url' => $payload['cancel_url'] ?? null,
+            'custom_data' => $metadata,
         ], static fn ($value) => $value !== null && $value !== '');
 
-        $response = $this->paddle->post('/checkout/links', $requestPayload);
+        $response = $this->paddle->post('/transactions', $requestPayload);
 
-        $checkoutUrl = Arr::get($response, 'data.url') ?? Arr::get($response, 'url');
-        $checkoutId = Arr::get($response, 'data.id') ?? Arr::get($response, 'id');
+        $checkoutUrl = Arr::get($response, 'data.checkout.url')
+            ?? Arr::get($response, 'checkout.url')
+            ?? Arr::get($response, 'data.url')
+            ?? Arr::get($response, 'url');
+        $checkoutId = Arr::get($response, 'data.checkout_id')
+            ?? Arr::get($response, 'data.checkout.id')
+            ?? Arr::get($response, 'checkout_id')
+            ?? Arr::get($response, 'checkout.id');
+        $transactionId = Arr::get($response, 'data.id') ?? Arr::get($response, 'id');
 
         if (! $checkoutUrl) {
             Log::warning('Paddle addon checkout response missing url', ['response' => $response]);
@@ -108,7 +113,7 @@ class EventAddonCheckoutService
             'quantity' => $quantity,
             'price_id' => $priceId,
             'checkout_id' => $checkoutId,
-            'transaction_id' => null,
+            'transaction_id' => $transactionId,
             'status' => 'pending',
             'metadata' => array_merge($metadata, [
                 'increments' => $increments,
@@ -126,8 +131,10 @@ class EventAddonCheckoutService
 
         return [
             'checkout_url' => $checkoutUrl,
-            'expires_at' => Arr::get($response, 'data.expires_at') ?? Arr::get($response, 'expires_at'),
-            'id' => $checkoutId,
+            'expires_at' => Arr::get($response, 'data.checkout.expires_at')
+                ?? Arr::get($response, 'data.expires_at')
+                ?? Arr::get($response, 'expires_at'),
+            'id' => $transactionId ?? $checkoutId,
         ];
     }
 
diff --git a/app/Services/GiftVouchers/GiftVoucherCheckoutService.php b/app/Services/GiftVouchers/GiftVoucherCheckoutService.php
index cc62701..5774bf9 100644
--- a/app/Services/GiftVouchers/GiftVoucherCheckoutService.php
+++ b/app/Services/GiftVouchers/GiftVoucherCheckoutService.php
@@ -2,6 +2,7 @@
 
 namespace App\Services\GiftVouchers;
 
+use App\Services\Paddle\Exceptions\PaddleException;
 use App\Services\Paddle\PaddleClient;
 use Illuminate\Support\Arr;
 use Illuminate\Support\Facades\App;
@@ -49,6 +50,8 @@ class GiftVoucherCheckoutService
             ]);
         }
 
+        $customerId = $this->ensureCustomerId($data['purchaser_email']);
+
         $payload = [
             'items' => [
                 [
@@ -56,7 +59,7 @@ class GiftVoucherCheckoutService
                     'quantity' => 1,
                 ],
             ],
-            'customer_email' => $data['purchaser_email'],
+            'customer_id' => $customerId,
             'custom_data' => array_filter([
                 'type' => 'gift_voucher',
                 'tier_key' => $tier['key'],
@@ -66,15 +69,18 @@ class GiftVoucherCheckoutService
                 'message' => $data['message'] ?? null,
                 'app_locale' => App::getLocale(),
             ]),
-            'success_url' => $data['success_url'] ?? route('marketing.success', ['locale' => App::getLocale(), 'type' => 'gift']),
-            'cancel_url' => $data['return_url'] ?? route('packages', ['locale' => App::getLocale()]),
         ];
 
-        $response = $this->client->post('/checkout/links', $payload);
+        $response = $this->client->post('/transactions', $payload);
 
         return [
-            'checkout_url' => Arr::get($response, 'data.url') ?? Arr::get($response, 'url'),
-            'expires_at' => Arr::get($response, 'data.expires_at') ?? Arr::get($response, 'expires_at'),
+            'checkout_url' => Arr::get($response, 'data.checkout.url')
+                ?? Arr::get($response, 'checkout.url')
+                ?? Arr::get($response, 'data.url')
+                ?? Arr::get($response, 'url'),
+            'expires_at' => Arr::get($response, 'data.checkout.expires_at')
+                ?? Arr::get($response, 'data.expires_at')
+                ?? Arr::get($response, 'expires_at'),
             'id' => Arr::get($response, 'data.id') ?? Arr::get($response, 'id'),
         ];
     }
@@ -97,4 +103,43 @@ class GiftVoucherCheckoutService
 
         return $tier;
     }
+
+    protected function ensureCustomerId(string $email): string
+    {
+        $payload = ['email' => $email];
+
+        try {
+            $response = $this->client->post('/customers', $payload);
+        } catch (PaddleException $exception) {
+            $customerId = $this->resolveExistingCustomerId($email, $exception);
+
+            if ($customerId) {
+                return $customerId;
+            }
+
+            throw $exception;
+        }
+
+        $customerId = Arr::get($response, 'data.id') ?? Arr::get($response, 'id');
+
+        if (! $customerId) {
+            throw new PaddleException('Failed to create Paddle customer.');
+        }
+
+        return $customerId;
+    }
+
+    protected function resolveExistingCustomerId(string $email, PaddleException $exception): ?string
+    {
+        if ($exception->status() !== 409 || Arr::get($exception->context(), 'error.code') !== 'customer_already_exists') {
+            return null;
+        }
+
+        $response = $this->client->get('/customers', [
+            'email' => $email,
+            'per_page' => 1,
+        ]);
+
+        return Arr::get($response, 'data.0.id') ?? Arr::get($response, 'data.0.customer_id');
+    }
 }
diff --git a/app/Services/Paddle/PaddleCheckoutService.php b/app/Services/Paddle/PaddleCheckoutService.php
index 9574232..028217c 100644
--- a/app/Services/Paddle/PaddleCheckoutService.php
+++ b/app/Services/Paddle/PaddleCheckoutService.php
@@ -5,7 +5,6 @@ namespace App\Services\Paddle;
 use App\Models\Package;
 use App\Models\Tenant;
 use Illuminate\Support\Arr;
-use Illuminate\Support\Facades\App;
 use Illuminate\Support\Facades\Log;
 
 class PaddleCheckoutService
@@ -22,15 +21,6 @@ class PaddleCheckoutService
     {
         $customerId = $this->customers->ensureCustomerId($tenant);
 
-        $successUrl = $options['success_url'] ?? route('marketing.success', [
-            'locale' => App::getLocale(),
-            'packageId' => $package->id,
-        ]);
-        $returnUrl = $options['return_url'] ?? route('packages', [
-            'locale' => App::getLocale(),
-            'highlight' => $package->slug,
-        ]);
-
         $customData = $this->buildMetadata(
             $tenant,
             $package,
@@ -46,21 +36,18 @@ class PaddleCheckoutService
                 ],
             ],
             'custom_data' => $customData,
-            'success_url' => $successUrl,
-            'cancel_url' => $returnUrl,
         ];
 
         if (! empty($options['discount_id'])) {
             $payload['discount_id'] = $options['discount_id'];
         }
 
-        if ($tenant->contact_email) {
-            $payload['customer_email'] = $tenant->contact_email;
-        }
+        $response = $this->client->post('/transactions', $payload);
 
-        $response = $this->client->post('/checkout/links', $payload);
-
-        $checkoutUrl = Arr::get($response, 'data.url') ?? Arr::get($response, 'url');
+        $checkoutUrl = Arr::get($response, 'data.checkout.url')
+            ?? Arr::get($response, 'checkout.url')
+            ?? Arr::get($response, 'data.url')
+            ?? Arr::get($response, 'url');
 
         if (! $checkoutUrl) {
             Log::warning('Paddle checkout response missing url', ['response' => $response]);
@@ -68,7 +55,9 @@ class PaddleCheckoutService
 
         return [
             'checkout_url' => $checkoutUrl,
-            'expires_at' => Arr::get($response, 'data.expires_at') ?? Arr::get($response, 'expires_at'),
+            'expires_at' => Arr::get($response, 'data.checkout.expires_at')
+                ?? Arr::get($response, 'data.expires_at')
+                ?? Arr::get($response, 'expires_at'),
             'id' => Arr::get($response, 'data.id') ?? Arr::get($response, 'id'),
         ];
     }
diff --git a/app/Support/SentryReporter.php b/app/Support/SentryReporter.php
new file mode 100644
index 0000000..b5ed045
--- /dev/null
+++ b/app/Support/SentryReporter.php
@@ -0,0 +1,87 @@
+<?php
+
+namespace App\Support;
+
+use Sentry\State\Scope;
+use Throwable;
+
+class SentryReporter
+{
+    private static ?\WeakMap $reported = null;
+
+    /**
+     * @param  array{tags?: array<string, string|int|null>, extra?: array<string, mixed>}  $context
+     */
+    public static function captureException(Throwable $exception, array $context = []): void
+    {
+        if (! self::shouldReport()) {
+            return;
+        }
+
+        if (self::wasReported($exception)) {
+            return;
+        }
+
+        self::markReported($exception);
+
+        if (! function_exists('\Sentry\withScope')) {
+            app('sentry')->captureException($exception);
+
+            return;
+        }
+
+        \Sentry\withScope(function (Scope $scope) use ($exception, $context): void {
+            self::applyContext($scope, $context);
+            app('sentry')->captureException($exception);
+        });
+    }
+
+    private static function shouldReport(): bool
+    {
+        return app()->bound('sentry') && ! empty(config('sentry.dsn'));
+    }
+
+    private static function wasReported(Throwable $exception): bool
+    {
+        $reported = self::reportedMap();
+
+        return $reported->offsetExists($exception);
+    }
+
+    private static function markReported(Throwable $exception): void
+    {
+        $reported = self::reportedMap();
+        $reported[$exception] = true;
+    }
+
+    private static function reportedMap(): \WeakMap
+    {
+        if (! self::$reported instanceof \WeakMap) {
+            self::$reported = new \WeakMap;
+        }
+
+        return self::$reported;
+    }
+
+    /**
+     * @param  array{tags?: array<string, string|int|null>, extra?: array<string, mixed>}  $context
+     */
+    private static function applyContext(Scope $scope, array $context): void
+    {
+        foreach (($context['tags'] ?? []) as $key => $value) {
+            if ($value === null || $value === '') {
+                continue;
+            }
+
+            $scope->setTag((string) $key, (string) $value);
+        }
+
+        foreach (($context['extra'] ?? []) as $key => $value) {
+            if ($value === null) {
+                continue;
+            }
+
+            $scope->setExtra((string) $key, $value);
+        }
+    }
+}
diff --git a/bootstrap/app.php b/bootstrap/app.php
index c5a7a23..441a578 100644
--- a/bootstrap/app.php
+++ b/bootstrap/app.php
@@ -36,12 +36,55 @@ return Application::configure(basePath: dirname(__DIR__))
         \App\Console\Commands\SeedDemoSwitcherTenants::class,
     ])
     ->withSchedule(function (\Illuminate\Console\Scheduling\Schedule $schedule) {
-        $schedule->command('package:check-status')->dailyAt('06:00');
-        $schedule->command('photobooth:cleanup-expired')->hourly()->withoutOverlapping();
-        $schedule->command('photobooth:ingest')->everyFiveMinutes()->withoutOverlapping();
-        $schedule->command('exports:purge')->dailyAt('02:00');
-        $schedule->command('tenants:retention-scan')->dailyAt('03:00');
-        $schedule->command('guest:feedback-reminders')->dailyAt('22:00');
+        $onFailure = static function (string $command): \Closure {
+            return static function () use ($command): void {
+                \App\Support\SentryReporter::captureException(
+                    new \RuntimeException('Scheduled command failed'),
+                    [
+                        'tags' => [
+                            'schedule_command' => $command,
+                        ],
+                    ],
+                );
+            };
+        };
+
+        $schedule->command('package:check-status')
+            ->dailyAt('06:00')
+            ->onFailure($onFailure('package:check-status'));
+        $schedule->command('storage:monitor')
+            ->everyFiveMinutes()
+            ->withoutOverlapping()
+            ->onFailure($onFailure('storage:monitor'));
+        $schedule->command('storage:check-upload-queues')
+            ->everyFiveMinutes()
+            ->withoutOverlapping()
+            ->onFailure($onFailure('storage:check-upload-queues'));
+        $schedule->command('storage:archive-pending')
+            ->dailyAt('01:00')
+            ->withoutOverlapping()
+            ->onFailure($onFailure('storage:archive-pending'));
+        $schedule->command('photobooth:cleanup-expired')
+            ->hourly()
+            ->withoutOverlapping()
+            ->onFailure($onFailure('photobooth:cleanup-expired'));
+        $schedule->command('photobooth:ingest')
+            ->everyFiveMinutes()
+            ->withoutOverlapping()
+            ->onFailure($onFailure('photobooth:ingest'));
+        $schedule->command('checkout:send-reminders')
+            ->hourly()
+            ->withoutOverlapping()
+            ->onFailure($onFailure('checkout:send-reminders'));
+        $schedule->command('exports:purge')
+            ->dailyAt('02:00')
+            ->onFailure($onFailure('exports:purge'));
+        $schedule->command('tenants:retention-scan')
+            ->dailyAt('03:00')
+            ->onFailure($onFailure('tenants:retention-scan'));
+        $schedule->command('guest:feedback-reminders')
+            ->dailyAt('22:00')
+            ->onFailure($onFailure('guest:feedback-reminders'));
     })
     ->withMiddleware(function (Middleware $middleware) {
         $middleware->trustProxies(
diff --git a/config/horizon.php b/config/horizon.php
index 1153f9d..f2fd0a0 100644
--- a/config/horizon.php
+++ b/config/horizon.php
@@ -98,6 +98,10 @@ return [
 
     'waits' => [
         'redis:default' => 60,
+        'redis:media-storage' => 60,
+        'redis:media-security' => 60,
+        'redis:notifications' => 60,
+        'redis:webhooks' => 60,
     ],
 
     /*
@@ -197,9 +201,22 @@ return [
     */
 
     'defaults' => [
-        'supervisor-1' => [
+        'supervisor-default' => [
             'connection' => 'redis',
-            'queue' => ['default'],
+            'queue' => ['default', 'notifications', 'webhooks'],
+            'balance' => 'auto',
+            'autoScalingStrategy' => 'time',
+            'maxProcesses' => 1,
+            'maxTime' => 0,
+            'maxJobs' => 0,
+            'memory' => 128,
+            'tries' => 1,
+            'timeout' => 60,
+            'nice' => 0,
+        ],
+        'supervisor-media' => [
+            'connection' => 'redis',
+            'queue' => ['media-storage', 'media-security'],
             'balance' => 'auto',
             'autoScalingStrategy' => 'time',
             'maxProcesses' => 1,
@@ -214,17 +231,25 @@ return [
 
     'environments' => [
         'production' => [
-            'supervisor-1' => [
+            'supervisor-default' => [
                 'maxProcesses' => 10,
                 'balanceMaxShift' => 1,
                 'balanceCooldown' => 3,
             ],
+            'supervisor-media' => [
+                'maxProcesses' => 3,
+                'balanceMaxShift' => 1,
+                'balanceCooldown' => 3,
+            ],
         ],
 
         'local' => [
-            'supervisor-1' => [
+            'supervisor-default' => [
                 'maxProcesses' => 3,
             ],
+            'supervisor-media' => [
+                'maxProcesses' => 1,
+            ],
         ],
     ],
 ];
diff --git a/docker-compose.dokploy.yml b/docker-compose.dokploy.yml
index ef602ca..f4e8c13 100644
--- a/docker-compose.dokploy.yml
+++ b/docker-compose.dokploy.yml
@@ -195,7 +195,7 @@ services:
     image: ${APP_IMAGE_REPO:-fotospiel-app}:${APP_IMAGE_TAG:-latest}
     env_file:
       - path: .env
-    command: /var/www/html/scripts/queue-worker.sh default
+    command: /var/www/html/scripts/queue-worker.sh default,notifications,webhooks
     environment:
       <<: *app-env
       SKIP_CODE_SYNC: "1"
@@ -237,6 +237,30 @@ services:
         condition: service_started
     restart: unless-stopped
 
+  media-security-worker:
+    image: ${APP_IMAGE_REPO:-fotospiel-app}:${APP_IMAGE_TAG:-latest}
+    env_file:
+      - path: .env
+    command: /var/www/html/scripts/queue-worker.sh media-security
+    environment:
+      <<: *app-env
+      QUEUE_TRIES: 3
+      QUEUE_SLEEP: 5
+      SKIP_CODE_SYNC: "1"
+    volumes:
+      - app-code:/var/www/html
+      - app-storage:/var/www/html/storage
+      - app-bootstrap-cache:/var/www/html/bootstrap/cache
+    networks:
+      - default
+      - photobooth-network
+    depends_on:
+      app:
+        condition: service_healthy
+      redis:
+        condition: service_started
+    restart: unless-stopped
+
   scheduler:
     image: ${APP_IMAGE_REPO:-fotospiel-app}:${APP_IMAGE_TAG:-latest}
     env_file:
diff --git a/resources/js/admin/api.ts b/resources/js/admin/api.ts
index 5d75450..b042fec 100644
--- a/resources/js/admin/api.ts
+++ b/resources/js/admin/api.ts
@@ -305,6 +305,8 @@ export type TenantOnboardingStatus = {
     admin_app_opened_at?: string | null;
     primary_event_id?: number | string | null;
     selected_packages?: unknown;
+    dismissed_at?: string | null;
+    completed_at?: string | null;
     branding_completed?: boolean;
     tasks_configured?: boolean;
     event_created?: boolean;
diff --git a/resources/js/admin/i18n/locales/de/management.json b/resources/js/admin/i18n/locales/de/management.json
index c98aff3..9845812 100644
--- a/resources/js/admin/i18n/locales/de/management.json
+++ b/resources/js/admin/i18n/locales/de/management.json
@@ -2217,6 +2217,24 @@
       "checkoutMissing": "Checkout konnte nicht gestartet werden.",
       "checkoutFailed": "Add-on Checkout fehlgeschlagen."
     },
+    "legalConsent": {
+      "title": "Vor dem Kauf",
+      "description": "Bitte bestätige die rechtlichen Hinweise, bevor du ein Add-on kaufst.",
+      "checkboxTerms": "Ich habe die AGB, die Datenschutzerklärung und die Widerrufsbelehrung gelesen und akzeptiere sie.",
+      "checkboxWaiver": "Ich verlange ausdrücklich, dass mit der Bereitstellung der digitalen Leistung (Aktivierung meines Event-Add-ons) vor Ablauf der Widerrufsfrist begonnen wird. Mir ist bekannt, dass ich mein Widerrufsrecht verliere, sobald der Vertrag vollständig erfüllt ist.",
+      "errorTerms": "Bitte bestätige AGB, Datenschutzerklärung und Widerrufsbelehrung.",
+      "errorWaiver": "Bitte bestätige den sofortigen Leistungsbeginn und das vorzeitige Erlöschen des Widerrufsrechts.",
+      "confirm": "Weiter zum Checkout",
+      "cancel": "Abbrechen"
+    },
+    "eventStartConsent": {
+      "title": "Vor dem ersten Event",
+      "description": "Bitte bestätige den sofortigen Beginn der digitalen Leistung, bevor du dein erstes Event erstellst.",
+      "checkboxWaiver": "Ich verlange ausdrücklich, dass mit der Bereitstellung der digitalen Leistung jetzt begonnen wird. Mir ist bekannt, dass ich mein Widerrufsrecht verliere, sobald der Vertrag vollständig erfüllt ist.",
+      "errorWaiver": "Bitte bestätige den sofortigen Leistungsbeginn und das vorzeitige Erlöschen des Widerrufsrechts.",
+      "confirm": "Event erstellen",
+      "cancel": "Abbrechen"
+    },
     "placeholders": {
       "untitled": "Unbenanntes Event"
     },
diff --git a/resources/js/admin/i18n/locales/en/management.json b/resources/js/admin/i18n/locales/en/management.json
index f261c3c..f0ec75e 100644
--- a/resources/js/admin/i18n/locales/en/management.json
+++ b/resources/js/admin/i18n/locales/en/management.json
@@ -2221,6 +2221,24 @@
       "checkoutMissing": "Checkout could not be started.",
       "checkoutFailed": "Add-on checkout failed."
     },
+    "legalConsent": {
+      "title": "Before purchase",
+      "description": "Please confirm the legal notes before buying an add-on.",
+      "checkboxTerms": "I have read and accept the Terms & Conditions, Privacy Policy, and Right of Withdrawal.",
+      "checkboxWaiver": "I expressly request that you begin providing the digital services (activation of my event add-on) before the withdrawal period has expired. I understand that I lose my right of withdrawal once the contract has been fully performed.",
+      "errorTerms": "Please confirm you accept the terms, privacy policy, and right of withdrawal.",
+      "errorWaiver": "Please confirm the immediate start of the digital service and the early expiry of the right of withdrawal.",
+      "confirm": "Continue to checkout",
+      "cancel": "Cancel"
+    },
+    "eventStartConsent": {
+      "title": "Before your first event",
+      "description": "Please confirm the immediate start of the digital service before creating your first event.",
+      "checkboxWaiver": "I expressly request that the digital service begins now and understand my right of withdrawal expires once the contract has been fully performed.",
+      "errorWaiver": "Please confirm the immediate start of the digital service and the early expiry of the right of withdrawal.",
+      "confirm": "Create event",
+      "cancel": "Cancel"
+    },
     "placeholders": {
       "untitled": "Untitled event"
     },
diff --git a/resources/js/admin/mobile/components/LegalConsentSheet.tsx b/resources/js/admin/mobile/components/LegalConsentSheet.tsx
index 5b9a6a4..bde1eb7 100644
--- a/resources/js/admin/mobile/components/LegalConsentSheet.tsx
+++ b/resources/js/admin/mobile/components/LegalConsentSheet.tsx
@@ -1,6 +1,7 @@
 import React from 'react';
 import { YStack } from '@tamagui/stacks';
 import { SizableText as Text } from '@tamagui/text';
+import { useTheme } from '@tamagui/core';
 import { MobileSheet } from './Sheet';
 import { CTAButton } from './Primitives';
 
@@ -36,9 +37,24 @@ export function LegalConsentSheet({
   copy,
   t,
 }: LegalConsentSheetProps) {
+  const theme = useTheme();
   const [acceptedTerms, setAcceptedTerms] = React.useState(false);
   const [acceptedWaiver, setAcceptedWaiver] = React.useState(false);
   const [error, setError] = React.useState<string | null>(null);
+  const checkboxAccent = String(theme.primary?.val ?? '#2563eb');
+  const checkboxBorder = String(theme.borderColor?.val ?? '#e5e7eb');
+  const checkboxSurface = String(theme.surface?.val ?? '#ffffff');
+  const checkboxStyle = {
+    marginTop: 4,
+    width: 18,
+    height: 18,
+    accentColor: checkboxAccent,
+    backgroundColor: checkboxSurface,
+    border: `1px solid ${checkboxBorder}`,
+    borderRadius: 4,
+    appearance: 'auto',
+    WebkitAppearance: 'auto',
+  } as const;
 
   React.useEffect(() => {
     if (open) {
@@ -103,7 +119,7 @@ export function LegalConsentSheet({
               type="checkbox"
               checked={acceptedTerms}
               onChange={(event) => setAcceptedTerms(event.target.checked)}
-              style={{ marginTop: 4, width: 16, height: 16 }}
+              style={checkboxStyle}
             />
             <Text fontSize="$sm" color="#111827">
               {copy?.checkboxTerms ?? t(
@@ -119,7 +135,7 @@ export function LegalConsentSheet({
               type="checkbox"
               checked={acceptedWaiver}
               onChange={(event) => setAcceptedWaiver(event.target.checked)}
-              style={{ marginTop: 4, width: 16, height: 16 }}
+              style={checkboxStyle}
             />
             <Text fontSize="$sm" color="#111827">
               {copy?.checkboxWaiver ?? t(
diff --git a/resources/js/admin/mobile/components/__tests__/LegalConsentSheet.test.tsx b/resources/js/admin/mobile/components/__tests__/LegalConsentSheet.test.tsx
new file mode 100644
index 0000000..3ace955
--- /dev/null
+++ b/resources/js/admin/mobile/components/__tests__/LegalConsentSheet.test.tsx
@@ -0,0 +1,41 @@
+import React from 'react';
+import { describe, expect, it, vi } from 'vitest';
+import { render } from '@testing-library/react';
+
+vi.mock('@tamagui/core', () => ({
+  useTheme: () => ({
+    primary: { val: '#2563eb' },
+    borderColor: { val: '#e5e7eb' },
+    surface: { val: '#ffffff' },
+  }),
+}));
+
+vi.mock('@tamagui/stacks', () => ({
+  YStack: ({ children }: { children: React.ReactNode }) => <div>{children}</div>,
+  XStack: ({ children }: { children: React.ReactNode }) => <div>{children}</div>,
+}));
+
+vi.mock('@tamagui/text', () => ({
+  SizableText: ({ children }: { children: React.ReactNode }) => <span>{children}</span>,
+}));
+
+vi.mock('@tamagui/react-native-web-lite', () => ({
+  Pressable: ({ children }: { children: React.ReactNode }) => <button type="button">{children}</button>,
+}));
+
+import { LegalConsentSheet } from '../LegalConsentSheet';
+
+describe('LegalConsentSheet', () => {
+  it('renders the required consent checkboxes when open', () => {
+    const { getAllByRole } = render(
+      <LegalConsentSheet
+        open
+        onClose={vi.fn()}
+        onConfirm={vi.fn()}
+        t={(key, fallback) => fallback ?? key}
+      />
+    );
+
+    expect(getAllByRole('checkbox')).toHaveLength(2);
+  });
+});
diff --git a/resources/js/admin/mobile/lib/onboardingGuard.test.ts b/resources/js/admin/mobile/lib/onboardingGuard.test.ts
index ea07121..dfe3c50 100644
--- a/resources/js/admin/mobile/lib/onboardingGuard.test.ts
+++ b/resources/js/admin/mobile/lib/onboardingGuard.test.ts
@@ -1,8 +1,8 @@
 import { describe, expect, it } from 'vitest';
 import { resolveOnboardingRedirect } from './onboardingGuard';
 import {
+  ADMIN_WELCOME_BASE_PATH,
   ADMIN_WELCOME_EVENT_PATH,
-  ADMIN_WELCOME_PACKAGES_PATH,
   ADMIN_WELCOME_SUMMARY_PATH,
 } from '../../constants';
 
@@ -15,6 +15,8 @@ describe('resolveOnboardingRedirect', () => {
       pathname: '/event-admin/mobile/dashboard',
       isWelcomePath: false,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
     expect(result).toBeNull();
   });
@@ -24,9 +26,11 @@ describe('resolveOnboardingRedirect', () => {
       hasEvents: false,
       hasActivePackage: false,
       selectedPackageId: null,
-      pathname: ADMIN_WELCOME_PACKAGES_PATH,
+      pathname: ADMIN_WELCOME_BASE_PATH,
       isWelcomePath: true,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
     expect(result).toBeNull();
   });
@@ -39,6 +43,8 @@ describe('resolveOnboardingRedirect', () => {
       pathname: '/event-admin/mobile/billing',
       isWelcomePath: false,
       isBillingPath: true,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
     expect(result).toBeNull();
   });
@@ -51,6 +57,8 @@ describe('resolveOnboardingRedirect', () => {
       pathname: '/event-admin/mobile/dashboard',
       isWelcomePath: false,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
     expect(result).toBe(ADMIN_WELCOME_EVENT_PATH);
   });
@@ -63,11 +71,13 @@ describe('resolveOnboardingRedirect', () => {
       pathname: '/event-admin/mobile/dashboard',
       isWelcomePath: false,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
     expect(result).toBe(ADMIN_WELCOME_SUMMARY_PATH);
   });
 
-  it('redirects to packages when no selection exists', () => {
+  it('redirects to landing when no selection exists', () => {
     const result = resolveOnboardingRedirect({
       hasEvents: false,
       hasActivePackage: false,
@@ -75,8 +85,10 @@ describe('resolveOnboardingRedirect', () => {
       pathname: '/event-admin/mobile/dashboard',
       isWelcomePath: false,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
     });
-    expect(result).toBe(ADMIN_WELCOME_PACKAGES_PATH);
+    expect(result).toBe(ADMIN_WELCOME_BASE_PATH);
   });
 
   it('does not redirect when already on target', () => {
@@ -84,9 +96,39 @@ describe('resolveOnboardingRedirect', () => {
       hasEvents: false,
       hasActivePackage: false,
       selectedPackageId: null,
-      pathname: ADMIN_WELCOME_PACKAGES_PATH,
+      pathname: ADMIN_WELCOME_BASE_PATH,
       isWelcomePath: false,
       isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: false,
+    });
+    expect(result).toBeNull();
+  });
+
+  it('does not redirect when onboarding is dismissed', () => {
+    const result = resolveOnboardingRedirect({
+      hasEvents: false,
+      hasActivePackage: false,
+      selectedPackageId: null,
+      pathname: '/event-admin/mobile/dashboard',
+      isWelcomePath: false,
+      isBillingPath: false,
+      isOnboardingDismissed: true,
+      isOnboardingCompleted: false,
+    });
+    expect(result).toBeNull();
+  });
+
+  it('does not redirect when onboarding is completed', () => {
+    const result = resolveOnboardingRedirect({
+      hasEvents: false,
+      hasActivePackage: false,
+      selectedPackageId: null,
+      pathname: '/event-admin/mobile/dashboard',
+      isWelcomePath: false,
+      isBillingPath: false,
+      isOnboardingDismissed: false,
+      isOnboardingCompleted: true,
     });
     expect(result).toBeNull();
   });
diff --git a/resources/js/admin/mobile/lib/onboardingGuard.ts b/resources/js/admin/mobile/lib/onboardingGuard.ts
index 3f4c440..d89fac5 100644
--- a/resources/js/admin/mobile/lib/onboardingGuard.ts
+++ b/resources/js/admin/mobile/lib/onboardingGuard.ts
@@ -1,6 +1,6 @@
 import {
+  ADMIN_WELCOME_BASE_PATH,
   ADMIN_WELCOME_EVENT_PATH,
-  ADMIN_WELCOME_PACKAGES_PATH,
   ADMIN_WELCOME_SUMMARY_PATH,
 } from '../../constants';
 
@@ -11,6 +11,8 @@ type OnboardingRedirectInput = {
   pathname: string;
   isWelcomePath: boolean;
   isBillingPath: boolean;
+  isOnboardingDismissed?: boolean;
+  isOnboardingCompleted?: boolean;
 };
 
 export function resolveOnboardingRedirect({
@@ -20,11 +22,17 @@ export function resolveOnboardingRedirect({
   pathname,
   isWelcomePath,
   isBillingPath,
+  isOnboardingDismissed,
+  isOnboardingCompleted,
 }: OnboardingRedirectInput): string | null {
   if (hasEvents) {
     return null;
   }
 
+  if (isOnboardingDismissed || isOnboardingCompleted) {
+    return null;
+  }
+
   if (isWelcomePath || isBillingPath) {
     return null;
   }
@@ -34,7 +42,7 @@ export function resolveOnboardingRedirect({
     ? ADMIN_WELCOME_EVENT_PATH
     : shouldContinueSummary
       ? ADMIN_WELCOME_SUMMARY_PATH
-      : ADMIN_WELCOME_PACKAGES_PATH;
+      : ADMIN_WELCOME_BASE_PATH;
 
   if (pathname === target) {
     return null;
diff --git a/resources/js/admin/mobile/welcome/WelcomeEventPage.tsx b/resources/js/admin/mobile/welcome/WelcomeEventPage.tsx
index 95b51f5..b903b28 100644
--- a/resources/js/admin/mobile/welcome/WelcomeEventPage.tsx
+++ b/resources/js/admin/mobile/welcome/WelcomeEventPage.tsx
@@ -8,7 +8,7 @@ import { SizableText as Text } from '@tamagui/text';
 import { OnboardingShell } from '../components/OnboardingShell';
 import { MobileCard, CTAButton } from '../components/Primitives';
 import { ADMIN_HOME_PATH, ADMIN_WELCOME_BASE_PATH, ADMIN_WELCOME_PACKAGES_PATH, ADMIN_WELCOME_SUMMARY_PATH, adminPath } from '../../constants';
-import { getTenantPackagesOverview } from '../../api';
+import { getTenantPackagesOverview, trackOnboarding } from '../../api';
 import { getSelectedPackageId } from '../lib/onboardingSelection';
 
 export default function WelcomeEventPage() {
@@ -24,6 +24,10 @@ export default function WelcomeEventPage() {
 
   const hasActivePackage =
     Boolean(overview?.activePackage) || Boolean(overview?.packages?.some((pkg) => pkg.active));
+  const handleSkip = React.useCallback(() => {
+    void trackOnboarding('dismissed');
+    navigate(ADMIN_HOME_PATH);
+  }, [navigate]);
 
   const backTarget = selectedId
     ? ADMIN_WELCOME_SUMMARY_PATH
@@ -40,7 +44,7 @@ export default function WelcomeEventPage() {
         'Fill in a few details, invite co-hosts, and open your guest gallery for the big day.',
       )}
       onBack={() => navigate(backTarget)}
-      onSkip={() => navigate(ADMIN_HOME_PATH)}
+      onSkip={handleSkip}
       skipLabel={t('layout.jumpToDashboard', 'Jump to dashboard')}
     >
       <MobileCard space="$3">
diff --git a/resources/js/admin/mobile/welcome/WelcomeLandingPage.tsx b/resources/js/admin/mobile/welcome/WelcomeLandingPage.tsx
index f0ec81a..f36c7d7 100644
--- a/resources/js/admin/mobile/welcome/WelcomeLandingPage.tsx
+++ b/resources/js/admin/mobile/welcome/WelcomeLandingPage.tsx
@@ -7,7 +7,7 @@ import { YStack, XStack } from '@tamagui/stacks';
 import { SizableText as Text } from '@tamagui/text';
 import { MobileCard, CTAButton, PillBadge } from '../components/Primitives';
 import { OnboardingShell } from '../components/OnboardingShell';
-import { getTenantPackagesOverview } from '../../api';
+import { getTenantPackagesOverview, trackOnboarding } from '../../api';
 import { useEventContext } from '../../context/EventContext';
 import {
   ADMIN_HOME_PATH,
@@ -29,6 +29,10 @@ export default function WelcomeLandingPage() {
 
   const hasActivePackage =
     Boolean(packagesData?.activePackage) || Boolean(packagesData?.packages?.some((pkg) => pkg.active));
+  const handleSkip = React.useCallback(() => {
+    void trackOnboarding('dismissed');
+    navigate(ADMIN_HOME_PATH);
+  }, [navigate]);
 
   return (
     <OnboardingShell
@@ -38,7 +42,7 @@ export default function WelcomeLandingPage() {
         'layout.subtitle',
         'Begin with an inspired introduction, secure your package, and craft the perfect guest gallery – all optimised for mobile hosts.',
       )}
-      onSkip={() => navigate(ADMIN_HOME_PATH)}
+      onSkip={handleSkip}
       skipLabel={t('layout.jumpToDashboard', 'Jump to dashboard')}
     >
       <MobileCard space="$3">
diff --git a/resources/js/admin/router.tsx b/resources/js/admin/router.tsx
index a95cb6a..e412879 100644
--- a/resources/js/admin/router.tsx
+++ b/resources/js/admin/router.tsx
@@ -14,7 +14,7 @@ import {
   ADMIN_PUBLIC_LANDING_PATH,
   ADMIN_WELCOME_BASE_PATH,
 } from './constants';
-import { getTenantPackagesOverview } from './api';
+import { fetchOnboardingStatus, getTenantPackagesOverview } from './api';
 import { getSelectedPackageId } from './mobile/lib/onboardingSelection';
 import { resolveOnboardingRedirect } from './mobile/lib/onboardingGuard';
 const AuthCallbackPage = React.lazy(() => import('./mobile/AuthCallbackPage'));
@@ -47,14 +47,15 @@ const MobileWelcomeSummaryPage = React.lazy(() => import('./mobile/welcome/Welco
 const MobileWelcomeEventPage = React.lazy(() => import('./mobile/welcome/WelcomeEventPage'));
 
 function RequireAuth() {
-  const { status } = useAuth();
+  const { status, user } = useAuth();
   const location = useLocation();
   const { hasEvents, isLoading: eventsLoading } = useEventContext();
   const selectedPackageId = getSelectedPackageId();
   const isWelcomePath = location.pathname.startsWith(ADMIN_WELCOME_BASE_PATH);
   const isBillingPath = location.pathname.startsWith(ADMIN_BILLING_PATH);
+  const isTenantAdmin = Boolean(user && user.role !== 'member');
   const shouldCheckPackages =
-    status === 'authenticated' && !eventsLoading && !hasEvents && !isWelcomePath && !isBillingPath;
+    status === 'authenticated' && isTenantAdmin && !eventsLoading && !hasEvents && !isWelcomePath && !isBillingPath;
 
   const { data: packagesData, isLoading: packagesLoading } = useQuery({
     queryKey: ['mobile', 'onboarding', 'packages-overview'],
@@ -63,8 +64,18 @@ function RequireAuth() {
     staleTime: 60_000,
   });
 
+  const { data: onboardingStatus, isLoading: onboardingLoading } = useQuery({
+    queryKey: ['mobile', 'onboarding', 'status'],
+    queryFn: fetchOnboardingStatus,
+    enabled: shouldCheckPackages,
+    staleTime: 60_000,
+  });
+
   const hasActivePackage =
     Boolean(packagesData?.activePackage) || Boolean(packagesData?.packages?.some((pkg) => pkg.active));
+  const isOnboardingDismissed = Boolean(onboardingStatus?.steps?.dismissed_at);
+  const isOnboardingCompleted = Boolean(onboardingStatus?.steps?.completed_at);
+  const shouldBlockOnboarding = shouldCheckPackages && onboardingLoading;
 
   const redirectTarget = resolveOnboardingRedirect({
     hasEvents,
@@ -73,6 +84,8 @@ function RequireAuth() {
     pathname: location.pathname,
     isWelcomePath,
     isBillingPath,
+    isOnboardingDismissed,
+    isOnboardingCompleted,
   });
 
   if (status === 'loading') {
@@ -87,7 +100,7 @@ function RequireAuth() {
     return <Navigate to={ADMIN_LOGIN_START_PATH} state={{ from: location }} replace />;
   }
 
-  if (!isWelcomePath && !isBillingPath && (eventsLoading || packagesLoading)) {
+  if (!isWelcomePath && !isBillingPath && (eventsLoading || packagesLoading || shouldBlockOnboarding)) {
     return (
       <div className="flex min-h-screen items-center justify-center text-sm text-muted-foreground">
         Bitte warten ...
diff --git a/tests/Feature/Api/Tenant/OnboardingStatusTest.php b/tests/Feature/Api/Tenant/OnboardingStatusTest.php
new file mode 100644
index 0000000..7956b9e
--- /dev/null
+++ b/tests/Feature/Api/Tenant/OnboardingStatusTest.php
@@ -0,0 +1,50 @@
+<?php
+
+namespace Tests\Feature\Api\Tenant;
+
+use Illuminate\Support\Arr;
+use Tests\Feature\Tenant\TenantTestCase;
+
+class OnboardingStatusTest extends TenantTestCase
+{
+    public function test_tenant_can_dismiss_onboarding(): void
+    {
+        $response = $this->authenticatedRequest('POST', '/api/v1/tenant/onboarding', [
+            'step' => 'dismissed',
+        ]);
+
+        $response->assertOk();
+
+        $this->tenant->refresh();
+
+        $dismissedAt = Arr::get($this->tenant->settings ?? [], 'onboarding.dismissed_at');
+
+        $this->assertNotNull($dismissedAt);
+
+        $show = $this->authenticatedRequest('GET', '/api/v1/tenant/onboarding');
+
+        $show->assertOk();
+        $show->assertJsonPath('steps.dismissed_at', $dismissedAt);
+    }
+
+    public function test_tenant_can_mark_onboarding_completed(): void
+    {
+        $response = $this->authenticatedRequest('POST', '/api/v1/tenant/onboarding', [
+            'step' => 'completed',
+            'meta' => [],
+        ]);
+
+        $response->assertOk();
+
+        $this->tenant->refresh();
+
+        $completedAt = Arr::get($this->tenant->settings ?? [], 'onboarding.completed_at');
+
+        $this->assertNotNull($completedAt);
+
+        $show = $this->authenticatedRequest('GET', '/api/v1/tenant/onboarding');
+
+        $show->assertOk();
+        $show->assertJsonPath('steps.completed_at', $completedAt);
+    }
+}
diff --git a/tests/Feature/Console/ScheduleConfigurationTest.php b/tests/Feature/Console/ScheduleConfigurationTest.php
new file mode 100644
index 0000000..261f9fe
--- /dev/null
+++ b/tests/Feature/Console/ScheduleConfigurationTest.php
@@ -0,0 +1,42 @@
+<?php
+
+namespace Tests\Feature\Console;
+
+use Illuminate\Support\Facades\Artisan;
+use Illuminate\Support\Str;
+use Tests\TestCase;
+
+class ScheduleConfigurationTest extends TestCase
+{
+    public function test_storage_and_checkout_commands_are_scheduled(): void
+    {
+        Artisan::call('schedule:list', [
+            '--json' => true,
+            '--no-interaction' => true,
+        ]);
+
+        $tasks = json_decode(Artisan::output(), true, 512, JSON_THROW_ON_ERROR);
+
+        $this->assertScheduledCommand($tasks, 'storage:monitor', '*/5 * * * *');
+        $this->assertScheduledCommand($tasks, 'storage:check-upload-queues', '*/5 * * * *');
+        $this->assertScheduledCommand($tasks, 'storage:archive-pending', '0 1 * * *');
+        $this->assertScheduledCommand($tasks, 'checkout:send-reminders', '0 * * * *');
+    }
+
+    /**
+     * @param  array<int, array<string, mixed>>  $tasks
+     */
+    private function assertScheduledCommand(array $tasks, string $command, string $expression): void
+    {
+        foreach ($tasks as $task) {
+            $taskCommand = (string) ($task['command'] ?? '');
+            if ($taskCommand !== '' && Str::contains($taskCommand, $command)) {
+                $this->assertSame($expression, $task['expression'] ?? null);
+
+                return;
+            }
+        }
+
+        $this->fail(sprintf('Scheduled command not found: %s', $command));
+    }
+}
diff --git a/tests/Feature/SentryReportingTest.php b/tests/Feature/SentryReportingTest.php
index 4aa1fcb..1bebc2b 100644
--- a/tests/Feature/SentryReportingTest.php
+++ b/tests/Feature/SentryReportingTest.php
@@ -2,6 +2,10 @@
 
 namespace Tests\Feature;
 
+use Illuminate\Console\Scheduling\Schedule;
+use Illuminate\Queue\Events\JobFailed;
+use Illuminate\Support\Facades\Artisan;
+use Illuminate\Support\Facades\Event;
 use Symfony\Component\HttpKernel\Exception\HttpException;
 use Tests\TestCase;
 
@@ -55,4 +59,156 @@ class SentryReportingTest extends TestCase
 
         $this->assertSame(0, $fake->captured, 'Sentry should ignore 4xx errors');
     }
+
+    public function test_reports_scheduled_task_failures_to_sentry(): void
+    {
+        $fake = new class
+        {
+            public int $captured = 0;
+
+            public function captureException(mixed $exception = null): void
+            {
+                $this->captured++;
+            }
+        };
+
+        $this->app->instance('sentry', $fake);
+
+        Artisan::call('schedule:list', [
+            '--json' => true,
+            '--no-interaction' => true,
+        ]);
+
+        $schedule = $this->app->make(Schedule::class);
+        $task = collect($schedule->events())
+            ->first(fn ($event) => str_contains((string) $event->command, 'storage:monitor'));
+
+        $this->assertNotNull($task, 'Expected scheduled storage:monitor task');
+
+        $task->finish($this->app, 1);
+
+        $this->assertSame(1, $fake->captured, 'Sentry should receive scheduled task failures');
+    }
+
+    public function test_reports_queue_failures_to_sentry(): void
+    {
+        $fake = new class
+        {
+            public int $captured = 0;
+
+            public function captureException(mixed $exception = null): void
+            {
+                $this->captured++;
+            }
+        };
+
+        $this->app->instance('sentry', $fake);
+
+        $job = new class implements \Illuminate\Contracts\Queue\Job
+        {
+            public function uuid(): ?string
+            {
+                return null;
+            }
+
+            public function getJobId(): string
+            {
+                return 'job-id';
+            }
+
+            public function payload(): array
+            {
+                return [];
+            }
+
+            public function fire(): void {}
+
+            public function release($delay = 0): void {}
+
+            public function isReleased(): bool
+            {
+                return false;
+            }
+
+            public function delete(): void {}
+
+            public function isDeleted(): bool
+            {
+                return false;
+            }
+
+            public function isDeletedOrReleased(): bool
+            {
+                return false;
+            }
+
+            public function attempts(): int
+            {
+                return 1;
+            }
+
+            public function hasFailed(): bool
+            {
+                return false;
+            }
+
+            public function markAsFailed(): void {}
+
+            public function fail($e = null): void {}
+
+            public function maxTries(): ?int
+            {
+                return null;
+            }
+
+            public function maxExceptions(): ?int
+            {
+                return null;
+            }
+
+            public function timeout(): ?int
+            {
+                return null;
+            }
+
+            public function retryUntil(): ?int
+            {
+                return null;
+            }
+
+            public function getName(): string
+            {
+                return 'FakeJob';
+            }
+
+            public function resolveName(): string
+            {
+                return 'FakeJob';
+            }
+
+            public function resolveQueuedJobClass(): string
+            {
+                return 'FakeJob';
+            }
+
+            public function getConnectionName(): string
+            {
+                return 'redis';
+            }
+
+            public function getQueue(): string
+            {
+                return 'default';
+            }
+
+            public function getRawBody(): string
+            {
+                return '{}';
+            }
+        };
+
+        Event::dispatch(new JobFailed('redis', $job, new \RuntimeException('Queue failure')));
+
+        $this->assertSame(1, $fake->captured, 'Sentry should receive queue failures');
+    }
 }
diff --git a/tests/Feature/Tenant/EventAddonCheckoutTest.php b/tests/Feature/Tenant/EventAddonCheckoutTest.php
index 1feffbe..95a2911 100644
--- a/tests/Feature/Tenant/EventAddonCheckoutTest.php
+++ b/tests/Feature/Tenant/EventAddonCheckoutTest.php
@@ -27,11 +27,17 @@ class EventAddonCheckoutTest extends TenantTestCase
 
         // Fake Paddle response
         Http::fake([
-            '*/checkout/links' => Http::response([
+            '*/customers' => Http::response([
                 'data' => [
-                    'url' => 'https://checkout.paddle.test/abcd',
-                    'id' => 'chk_addon_123',
-                    'expires_at' => now()->addHour()->toIso8601String(),
+                    'id' => 'ctm_addon_123',
+                ],
+            ], 200),
+            '*/transactions' => Http::response([
+                'data' => [
+                    'id' => 'txn_addon_123',
+                    'checkout' => [
+                        'url' => 'https://checkout.paddle.test/abcd',
+                    ],
                 ],
             ], 200),
         ]);
@@ -67,14 +73,14 @@ class EventAddonCheckoutTest extends TenantTestCase
         ]);
 
         $response->assertOk();
-        $response->assertJsonPath('checkout_id', 'chk_addon_123');
+        $response->assertJsonPath('checkout_id', 'txn_addon_123');
 
         $this->assertDatabaseHas('event_package_addons', [
             'event_package_id' => $eventPackage->id,
             'addon_key' => 'extra_photos_small',
             'status' => 'pending',
             'quantity' => 2,
-            'checkout_id' => 'chk_addon_123',
+            'transaction_id' => 'txn_addon_123',
         ]);
 
         $addon = EventPackageAddon::where('event_package_id', $eventPackage->id)->latest()->first();
diff --git a/tests/Unit/GiftVoucherCheckoutServiceTest.php b/tests/Unit/GiftVoucherCheckoutServiceTest.php
index e395ae7..39d8f67 100644
--- a/tests/Unit/GiftVoucherCheckoutServiceTest.php
+++ b/tests/Unit/GiftVoucherCheckoutServiceTest.php
@@ -37,12 +37,18 @@ class GiftVoucherCheckoutServiceTest extends TestCase
         $client = Mockery::mock(PaddleClient::class);
         $client->shouldReceive('post')
             ->once()
-            ->with('/checkout/links', Mockery::on(function ($payload) {
+            ->with('/customers', Mockery::on(function ($payload) {
+                return $payload['email'] === 'buyer@example.com';
+            }))
+            ->andReturn(['data' => ['id' => 'ctm_123']]);
+        $client->shouldReceive('post')
+            ->once()
+            ->with('/transactions', Mockery::on(function ($payload) {
                 return $payload['items'][0]['price_id'] === 'pri_a'
-                    && $payload['customer_email'] === 'buyer@example.com'
+                    && $payload['customer_id'] === 'ctm_123'
                     && $payload['custom_data']['type'] === 'gift_voucher';
             }))
-            ->andReturn(['data' => ['url' => 'https://paddle.test/checkout/123', 'expires_at' => '2025-12-31T00:00:00Z', 'id' => 'chk_123']]);
+            ->andReturn(['data' => ['checkout' => ['url' => 'https://paddle.test/checkout/123'], 'id' => 'txn_123']]);
 
         $this->app->instance(PaddleClient::class, $client);
 
@@ -57,6 +63,6 @@ class GiftVoucherCheckoutServiceTest extends TestCase
         ]);
 
         $this->assertSame('https://paddle.test/checkout/123', $checkout['checkout_url']);
-        $this->assertSame('chk_123', $checkout['id']);
+        $this->assertSame('txn_123', $checkout['id']);
     }
 }
diff --git a/tests/Unit/PaddleCheckoutServiceTest.php b/tests/Unit/PaddleCheckoutServiceTest.php
index 769303a..f0528f3 100644
--- a/tests/Unit/PaddleCheckoutServiceTest.php
+++ b/tests/Unit/PaddleCheckoutServiceTest.php
@@ -35,15 +35,18 @@ class PaddleCheckoutServiceTest extends TestCase
 
         $client->shouldReceive('post')
             ->once()
-            ->with('/checkout/links', Mockery::on(function (array $payload) use ($tenant, $package) {
+            ->with('/transactions', Mockery::on(function (array $payload) use ($tenant, $package) {
                 return $payload['items'][0]['price_id'] === 'pri_123'
                     && $payload['customer_id'] === 'ctm_123'
                     && ($payload['custom_data']['tenant_id'] ?? null) === (string) $tenant->id
                     && ($payload['custom_data']['package_id'] ?? null) === (string) $package->id
                     && ($payload['custom_data']['source'] ?? null) === 'test'
-                    && ! isset($payload['metadata']);
+                    && ! isset($payload['metadata'])
+                    && ! isset($payload['success_url'])
+                    && ! isset($payload['cancel_url'])
+                    && ! isset($payload['customer_email']);
             }))
-            ->andReturn(['data' => ['url' => 'https://paddle.test/checkout/123', 'id' => 'chk_123']]);
+            ->andReturn(['data' => ['checkout' => ['url' => 'https://paddle.test/checkout/123'], 'id' => 'txn_123']]);
 
         $this->app->instance(PaddleClient::class, $client);
         $this->app->instance(PaddleCustomerService::class, $customers);
@@ -57,6 +60,6 @@ class PaddleCheckoutServiceTest extends TestCase
         ]);
 
         $this->assertSame('https://paddle.test/checkout/123', $checkout['checkout_url']);
-        $this->assertSame('chk_123', $checkout['id']);
+        $this->assertSame('txn_123', $checkout['id']);
     }
 }