api/app/Enums/Observability/ActorType.php

@@ -15,9 +15,13 @@ use Illuminate\Http\Request;
  *  1. Portal-token request → PORTAL_TOKEN
  *  2. Authenticated super_admin → SUPER_ADMIN
  *  3. Authenticated org_admin → ORGANIZER_ADMIN
- *  4. Authenticated volunteer (role match) → VOLUNTEER
- *  5. Other authenticated user → ORG_MEMBER
- *  6. None of the above → UNAUTHENTICATED
+ *  4. Other authenticated user → ORG_MEMBER (covers volunteers — Crewli has
+ *     no `volunteer` Spatie role today; volunteers join an organisation as
+ *     org_member with org-pivot semantics. Promote to a dedicated case once
+ *     the role model differentiates them at the user level.)
+ *  5. None of the above → UNAUTHENTICATED
+ *
+ * The VOLUNTEER case is reserved for that future split.
  */
 enum ActorType: string
 {
@@ -46,10 +50,6 @@ enum ActorType: string
             return self::ORGANIZER_ADMIN;
         }
 
-        if ($user->hasRole('volunteer')) {
-            return self::VOLUNTEER;
-        }
-
         return self::ORG_MEMBER;
     }
 }

api/app/Http/Middleware/BindSentryContext.php

@@ -0,0 +1,195 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Http\Middleware;
+
+use App\Enums\Observability\ActorType;
+use App\Models\Event;
+use App\Models\ImpersonationSession;
+use App\Models\Organisation;
+use App\Models\User;
+use Closure;
+use Illuminate\Http\Request;
+use Illuminate\Support\Facades\Log;
+use RuntimeException;
+use Sentry\State\Scope;
+use Symfony\Component\HttpFoundation\Response;
+
+use function Sentry\configureScope;
+
+/**
+ * Attach the Crewli context tags listed in RFC-WS-7 §3.6 to every Sentry
+ * event captured during this request.
+ *
+ * Multi-tenant invariant (§3.6): if the request is authenticated AND a
+ * controller is about to act on tenant data, organisation_id MUST be
+ * resolvable. In `local` and `testing` we throw so missing-tag bugs surface
+ * during development; in other environments we log a warning and fall
+ * through (don't break user flows over a missing tag).
+ */
+final class BindSentryContext
+{
+    public function handle(Request $request, Closure $next): Response
+    {
+        $user = $request->user();
+        $actorType = ActorType::resolve($user, $request);
+        $organisationId = $this->resolveOrganisationId($request);
+        $eventId = $this->resolveEventId($request);
+        $impersonatorUserId = $this->resolveImpersonatorUserId($request);
+
+        $this->enforceTenantInvariant($request, $user, $organisationId);
+
+        configureScope(function (Scope $scope) use ($request, $user, $actorType, $organisationId, $eventId, $impersonatorUserId): void {
+            $scope->setTag('app', 'api');
+            $scope->setTag('http.method', $request->method());
+            $scope->setTag('actor_type', $actorType->value);
+
+            $routeName = $request->route()?->getName();
+            if (is_string($routeName) && $routeName !== '') {
+                $scope->setTag('route_name', $routeName);
+            }
+
+            if ($user instanceof User) {
+                $scope->setTag('user_id', $user->id);
+                $scope->setUser([
+                    'id' => $user->id,
+                    'username' => $user->id,
+                ]);
+            }
+
+            if (is_string($organisationId) && $organisationId !== '') {
+                $scope->setTag('organisation_id', $organisationId);
+            }
+
+            if (is_string($eventId) && $eventId !== '') {
+                $scope->setTag('event_id', $eventId);
+            }
+
+            $scope->setTag('impersonation.active', $impersonatorUserId !== null ? 'true' : 'false');
+            if ($impersonatorUserId !== null) {
+                $scope->setTag('impersonation.impersonator_user_id', $impersonatorUserId);
+            }
+        });
+
+        return $next($request);
+    }
+
+    private function resolveOrganisationId(Request $request): ?string
+    {
+        $portalEvent = $request->attributes->get('portal_event');
+        if ($portalEvent instanceof Event) {
+            return $portalEvent->organisation_id;
+        }
+
+        $route = $request->route();
+        if ($route === null) {
+            return null;
+        }
+
+        $org = $route->parameter('organisation');
+        if ($org instanceof Organisation) {
+            return $org->id;
+        }
+        if (is_string($org) && $org !== '') {
+            return $org;
+        }
+
+        $event = $route->parameter('event');
+        if ($event instanceof Event) {
+            return $event->organisation_id;
+        }
+
+        return null;
+    }
+
+    private function resolveEventId(Request $request): ?string
+    {
+        $portalEvent = $request->attributes->get('portal_event');
+        if ($portalEvent instanceof Event) {
+            return $portalEvent->id;
+        }
+
+        $event = $request->route()?->parameter('event');
+        if ($event instanceof Event) {
+            return $event->id;
+        }
+        if (is_string($event) && $event !== '') {
+            return $event;
+        }
+
+        return null;
+    }
+
+    private function resolveImpersonatorUserId(Request $request): ?string
+    {
+        $impersonator = $request->attributes->get('impersonator');
+        if ($impersonator instanceof User) {
+            return $impersonator->id;
+        }
+
+        $session = $request->attributes->get('impersonation_session');
+        if ($session instanceof ImpersonationSession) {
+            return $session->admin_id;
+        }
+
+        return null;
+    }
+
+    private function enforceTenantInvariant(Request $request, mixed $user, ?string $organisationId): void
+    {
+        if (! $user instanceof User) {
+            return;
+        }
+
+        if ($organisationId !== null) {
+            return;
+        }
+
+        if ($this->routeRequiresTenantContext($request) === false) {
+            return;
+        }
+
+        $env = app()->environment();
+        $message = sprintf(
+            'BindSentryContext: authenticated request to "%s" lacks resolvable organisation_id',
+            $request->path(),
+        );
+
+        if (in_array($env, ['local', 'testing'], true)) {
+            throw new RuntimeException($message);
+        }
+
+        Log::warning($message, [
+            'route' => $request->route()?->getName(),
+            'user_id' => $user->id,
+        ]);
+    }
+
+    /**
+     * The Crewli tenant invariant: a route that declares an `{organisation}`
+     * or `{event}` URI parameter MUST resolve to a real organisation_id by
+     * the time this middleware runs. Routes that don't declare those params
+     * are user-scoped (account, portal, lists across user's memberships) and
+     * legitimately have no tenant context.
+     */
+    private function routeRequiresTenantContext(Request $request): bool
+    {
+        if ($request->attributes->get('portal_event') !== null) {
+            return true;
+        }
+
+        $route = $request->route();
+        if ($route === null) {
+            // Synthetic test requests without a Laravel route still trigger
+            // the invariant if the path looks tenant-scoped, so dev-time
+            // bugs surface in unit/feature tests.
+            return str_contains($request->path(), 'organisations/')
+                || str_contains($request->path(), 'events/');
+        }
+
+        $names = $route->parameterNames();
+
+        return in_array('organisation', $names, true) || in_array('event', $names, true);
+    }
+}

api/app/Listeners/Observability/TagJobAttemptOnSentry.php

@@ -0,0 +1,29 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Listeners\Observability;
+
+use Illuminate\Queue\Events\JobProcessing;
+use Sentry\State\Scope;
+
+use function Sentry\configureScope;
+
+/**
+ * Listener for {@see JobProcessing} that attaches the `queue.attempt` tag
+ * (RFC-WS-7 §3.6) to the active Sentry scope before the job runs. Default
+ * stack-trace grouping is preserved — RFC §3.11 explicitly forbids
+ * per-attempt fingerprinting so retries that eventually succeed remain
+ * grouped with retries that always fail.
+ */
+final class TagJobAttemptOnSentry
+{
+    public function handle(JobProcessing $event): void
+    {
+        $attempt = (string) $event->job->attempts();
+
+        configureScope(static function (Scope $scope) use ($attempt): void {
+            $scope->setTag('queue.attempt', $attempt);
+        });
+    }
+}

api/app/Providers/AppServiceProvider.php

@@ -196,6 +196,14 @@ class AppServiceProvider extends ServiceProvider
             ApplyBindingsOnFormSectionSubmitted::class,
         );
 
+        // RFC-WS-7 §3.6 / §3.11 — tag captured Sentry events with the queue
+        // attempt count. Default stack-trace grouping is preserved (no
+        // per-attempt fingerprinting).
+        \Illuminate\Support\Facades\Event::listen(
+            \Illuminate\Queue\Events\JobProcessing::class,
+            \App\Listeners\Observability\TagJobAttemptOnSentry::class,
+        );
+
         ResetPassword::createUrlUsing(function ($user, string $token) {
             return config('crewli.portal_url').'/wachtwoord-resetten?token='.$token.'&email='.urlencode($user->email);
         });

api/bootstrap/app.php

@@ -36,6 +36,11 @@ return Application::configure(basePath: dirname(__DIR__))
             'portal.token' => \App\Http\Middleware\PortalTokenMiddleware::class,
             'role' => \Spatie\Permission\Middleware\RoleMiddleware::class,
             'impersonation' => \App\Http\Middleware\HandleImpersonation::class,
+            // RFC-WS-7 §3.6 — applied inside auth:sanctum groups so it runs
+            // after authentication and can read $request->user(). Cannot live
+            // on the api group because route-level auth middleware runs after
+            // group middleware in Laravel.
+            'sentry.context' => \App\Http\Middleware\BindSentryContext::class,
         ]);
     })
     ->withExceptions(function (Exceptions $exceptions): void {

api/routes/api.php

@@ -120,7 +120,7 @@ Route::middleware('throttle:30,1')->group(function (): void {
 
 // Platform Admin routes
 Route::prefix('admin')
-    ->middleware(['auth:sanctum', 'impersonation', 'role:super_admin'])
+    ->middleware(['auth:sanctum', 'impersonation', 'sentry.context', 'role:super_admin'])
     ->name('admin.')
     ->group(function () {
         // Organisations
@@ -155,7 +155,7 @@ Route::prefix('admin')
     });
 
 // Protected routes
-Route::middleware(['auth:sanctum', 'impersonation'])->group(function () {
+Route::middleware(['auth:sanctum', 'impersonation', 'sentry.context'])->group(function () {
     // Impersonation (stop — accessible by impersonated user, not just super_admin)
     Route::post('admin/stop-impersonation', [AdminImpersonationController::class, 'stop']);
 

api/tests/Feature/Observability/BindSentryContextTest.php

@@ -0,0 +1,329 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Tests\Feature\Observability;
+
+use App\Http\Middleware\BindSentryContext;
+use App\Models\Event;
+use App\Models\ImpersonationSession;
+use App\Models\Organisation;
+use App\Models\User;
+use Database\Seeders\RoleSeeder;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Http\Request;
+use RuntimeException;
+use Sentry\Event as SentryEvent;
+use Sentry\SentrySdk;
+use Sentry\State\Scope;
+use Tests\TestCase;
+
+use function Sentry\configureScope;
+
+final class BindSentryContextTest extends TestCase
+{
+    use RefreshDatabase;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+        $this->seed(RoleSeeder::class);
+        $this->resetSentryScope();
+    }
+
+    private function resetSentryScope(): void
+    {
+        SentrySdk::getCurrentHub()->pushScope();
+    }
+
+    /**
+     * Read the current Sentry scope by applying it to a fresh Event and
+     * harvesting the tags / user context.
+     *
+     * @return array{tags: array<string, string>, user: ?array<string, mixed>}
+     */
+    private function captureScope(): array
+    {
+        $event = SentryEvent::createEvent();
+
+        configureScope(static function (Scope $scope) use ($event): void {
+            $scope->applyToEvent($event);
+        });
+
+        $userBag = $event->getUser();
+
+        return [
+            'tags' => $event->getTags(),
+            'user' => $userBag === null ? null : array_filter([
+                'id' => $userBag->getId(),
+                'username' => $userBag->getUsername(),
+            ], static fn ($v) => $v !== null),
+        ];
+    }
+
+    private function runMiddleware(Request $request): void
+    {
+        (new BindSentryContext)->handle($request, static fn (Request $req) => response('ok'));
+    }
+
+    private function makeAuthenticatedRequest(User $user, string $path = 'api/v1/me/profile'): Request
+    {
+        $request = Request::create('http://localhost/'.$path, 'GET');
+        $request->setUserResolver(static fn () => $user);
+
+        return $request;
+    }
+
+    public function test_authenticated_org_admin_request_tags_organisation_id(): void
+    {
+        $org = Organisation::factory()->create();
+        $user = User::factory()->create();
+        $org->users()->attach($user, ['role' => 'org_admin']);
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/organisations/'.$org->id.'/some-path');
+        $request->setRouteResolver(function () use ($org, $request) {
+            $route = new \Illuminate\Routing\Route(['GET'], 'organisations/{organisation}/some-path', static fn () => null);
+            $route->bind($request);
+            $route->setParameter('organisation', $org);
+            $route->name('organisations.test');
+
+            return $route;
+        });
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame($org->id, $scope['tags']['organisation_id'] ?? null);
+    }
+
+    public function test_authenticated_org_admin_request_tags_user_id(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/me/profile');
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame($user->id, $scope['tags']['user_id'] ?? null);
+        $this->assertSame($user->id, $scope['user']['id'] ?? null);
+        $this->assertSame($user->id, $scope['user']['username'] ?? null);
+    }
+
+    public function test_authenticated_org_admin_request_tags_actor_type_organizer_admin(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('organizer_admin', $scope['tags']['actor_type'] ?? null);
+    }
+
+    public function test_super_admin_request_tags_actor_type_super_admin(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('super_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/admin/organisations');
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('super_admin', $scope['tags']['actor_type'] ?? null);
+    }
+
+    public function test_org_member_authenticated_user_tags_actor_type_org_member(): void
+    {
+        // Crewli has no `volunteer` Spatie role today; volunteers fall into
+        // org_member. The VOLUNTEER ActorType case is reserved for a future
+        // split — see ActorType::resolve() docblock.
+        $user = User::factory()->create();
+        $user->assignRole('org_member');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/me/profile');
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('org_member', $scope['tags']['actor_type'] ?? null);
+    }
+
+    public function test_portal_token_request_tags_actor_type_portal_token(): void
+    {
+        $org = Organisation::factory()->create();
+        $event = Event::factory()->create(['organisation_id' => $org->id]);
+
+        $request = Request::create('http://localhost/api/v1/portal/me', 'GET');
+        $request->attributes->set('portal_context', 'artist');
+        $request->attributes->set('portal_event', $event);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('portal_token', $scope['tags']['actor_type'] ?? null);
+    }
+
+    public function test_portal_token_request_tags_organisation_id_from_token(): void
+    {
+        $org = Organisation::factory()->create();
+        $event = Event::factory()->create(['organisation_id' => $org->id]);
+
+        $request = Request::create('http://localhost/api/v1/portal/me', 'GET');
+        $request->attributes->set('portal_context', 'artist');
+        $request->attributes->set('portal_event', $event);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame($org->id, $scope['tags']['organisation_id'] ?? null);
+        $this->assertSame($event->id, $scope['tags']['event_id'] ?? null);
+    }
+
+    public function test_unauthenticated_request_tags_actor_type_unauthenticated(): void
+    {
+        $request = Request::create('http://localhost/api/v1/auth/login', 'POST');
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('unauthenticated', $scope['tags']['actor_type'] ?? null);
+        $this->assertArrayNotHasKey('user_id', $scope['tags']);
+    }
+
+    public function test_authenticated_request_to_tenant_scoped_route_without_org_throws_in_test_environment(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/organisations/missing/events');
+        // Synthesise a route that DECLARES {organisation} but has no
+        // bound parameter — the invariant must fire.
+        $route = new \Illuminate\Routing\Route(['GET'], 'organisations/{organisation}/events', static fn () => null);
+        $route->bind($request);
+        $request->setRouteResolver(static fn () => $route);
+
+        $this->expectException(RuntimeException::class);
+        $this->expectExceptionMessageMatches('/lacks resolvable organisation_id/');
+
+        $this->runMiddleware($request);
+    }
+
+    public function test_authenticated_request_to_user_scoped_route_skips_invariant(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        // /me/profile route declares no {organisation} or {event} param —
+        // user-scoped, invariant skipped.
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/me/profile');
+        $route = new \Illuminate\Routing\Route(['GET'], 'me/profile', static fn () => null);
+        $route->bind($request);
+        $request->setRouteResolver(static fn () => $route);
+
+        $this->runMiddleware($request);
+
+        $scope = $this->captureScope();
+        $this->assertSame('organizer_admin', $scope['tags']['actor_type'] ?? null);
+    }
+
+    public function test_impersonation_active_tag_when_session_active(): void
+    {
+        $admin = User::factory()->create();
+        $admin->assignRole('super_admin');
+        $target = User::factory()->create();
+        $target->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($target, 'api/v1/me/profile');
+        $request->attributes->set('impersonator', $admin);
+        $session = new ImpersonationSession;
+        $session->id = '01J0000000000000000000IMPS';
+        $session->admin_id = $admin->id;
+        $session->target_user_id = $target->id;
+        $request->attributes->set('impersonation_session', $session);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('true', $scope['tags']['impersonation.active'] ?? null);
+    }
+
+    public function test_impersonation_impersonator_user_id_tag_when_session_active(): void
+    {
+        $admin = User::factory()->create();
+        $admin->assignRole('super_admin');
+        $target = User::factory()->create();
+        $target->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($target, 'api/v1/me/profile');
+        $request->attributes->set('impersonator', $admin);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame($admin->id, $scope['tags']['impersonation.impersonator_user_id'] ?? null);
+    }
+
+    public function test_impersonation_active_false_when_no_session(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/me/profile');
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('false', $scope['tags']['impersonation.active'] ?? null);
+        $this->assertArrayNotHasKey('impersonation.impersonator_user_id', $scope['tags']);
+    }
+
+    public function test_route_name_tag_present(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user, 'api/v1/me/profile');
+        $route = new \Illuminate\Routing\Route(['GET'], 'me/profile', static fn () => null);
+        $route->name('me.profile');
+        $route->bind($request);
+        $request->setRouteResolver(static fn () => $route);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('me.profile', $scope['tags']['route_name'] ?? null);
+    }
+
+    public function test_http_method_tag_present(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = Request::create('http://localhost/api/v1/me/profile', 'PATCH');
+        $request->setUserResolver(static fn () => $user);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('PATCH', $scope['tags']['http.method'] ?? null);
+    }
+
+    public function test_app_tag_is_api(): void
+    {
+        $user = User::factory()->create();
+        $user->assignRole('org_admin');
+
+        $request = $this->makeAuthenticatedRequest($user);
+
+        $this->runMiddleware($request);
+        $scope = $this->captureScope();
+
+        $this->assertSame('api', $scope['tags']['app'] ?? null);
+    }
+}