diff --git a/src/app/Handlers/Activesync.php b/src/app/Handlers/Activesync.php
index 9864c934..0937ffae 100644
--- a/src/app/Handlers/Activesync.php
+++ b/src/app/Handlers/Activesync.php
@@ -1,43 +1,58 @@
 <?php
 
 namespace App\Handlers;
 
+use App\Entitlement;
+use App\Sku;
+
 class Activesync extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
+    /**
+     * Handle entitlement creation event.
+     */
+    public static function entitlementCreated(Entitlement $entitlement): void
+    {
+        if (\config('app.with_ldap')) {
+            \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+        }
+    }
+
+    /**
+     * Handle entitlement deletion event.
+     */
+    public static function entitlementDeleted(Entitlement $entitlement): void
+    {
+        if (\config('app.with_ldap')) {
+            \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+        }
+    }
+
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
-    public static function metadata(\App\Sku $sku): array
+    public static function metadata(Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['required'] = ['Groupware'];
 
         return $data;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 70;
     }
 }
diff --git a/src/app/Handlers/Auth2F.php b/src/app/Handlers/Auth2F.php
index d2d067ae..8db1efde 100644
--- a/src/app/Handlers/Auth2F.php
+++ b/src/app/Handlers/Auth2F.php
@@ -1,58 +1,65 @@
 <?php
 
 namespace App\Handlers;
 
 use App\Entitlement;
+use App\Sku;
 
 class Auth2F extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
+    /**
+     * Handle entitlement creation event.
+     */
+    public static function entitlementCreated(Entitlement $entitlement): void
+    {
+        if (\config('app.with_ldap')) {
+            \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+        }
+    }
+
     /**
      * Handle entitlement deletion event.
      */
     public static function entitlementDeleted(Entitlement $entitlement): void
     {
         // Remove all configured 2FA methods from Roundcube database
         if ($entitlement->entitleable && !$entitlement->entitleable->trashed()) {
             // TODO: This should be an async job
             $sf = new \App\Auth\SecondFactor($entitlement->entitleable);
             $sf->removeFactors();
+
+            if (\config('app.with_ldap')) {
+                \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+            }
         }
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
-    public static function metadata(\App\Sku $sku): array
+    public static function metadata(Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['forbidden'] = ['Activesync'];
 
         return $data;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 60;
     }
 }
diff --git a/src/app/Handlers/Base.php b/src/app/Handlers/Base.php
index 5f17b358..aa47d8d7 100644
--- a/src/app/Handlers/Base.php
+++ b/src/app/Handlers/Base.php
@@ -1,119 +1,102 @@
 <?php
 
 namespace App\Handlers;
 
 use App\Entitlement;
+use App\Sku;
 
 abstract class Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return '';
     }
 
     /**
      * Handle entitlement creation event.
      */
     public static function entitlementCreated(Entitlement $entitlement): void
     {
         // NOP
     }
 
     /**
      * Handle entitlement deletion event.
      */
     public static function entitlementDeleted(Entitlement $entitlement): void
     {
         // NOP
     }
 
     /**
      * Check if the SKU is available to the user. An SKU is available
      * to the user/domain when either it is active or there's already an
      * active entitlement.
-     *
-     * @param \App\Sku  $sku    The SKU
-     * @param object    $object The entitleable object
-     *
-     * @return bool
      */
-    public static function isAvailable(\App\Sku $sku, $object): bool
+    public static function isAvailable(Sku $sku, $object): bool
     {
         if (!$sku->active) {
             if (!$object->entitlements()->where('sku_id', $sku->id)->first()) {
                 return false;
             }
         }
 
         return true;
     }
 
     /**
      * Metadata of this SKU handler.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
-    public static function metadata(\App\Sku $sku): array
+    public static function metadata(Sku $sku): array
     {
         return [
             // entitleable type
             'type' => \lcfirst(\class_basename(static::entitleableClass())),
             // handler
             'handler' => str_replace("App\\Handlers\\", '', static::class),
             // readonly entitlement state cannot be changed
             'readonly' => false,
             // is entitlement enabled by default?
             'enabled' => false,
             // priority on the entitlements list
             'prio' => static::priority(),
         ];
     }
 
     /**
      * Prerequisites for the Entitlement to be applied to the object.
-     *
-     * @param \App\Entitlement $entitlement
-     * @param mixed $object
-     *
-     * @return bool
      */
-    public static function preReq($entitlement, $object): bool
+    public static function preReq(Entitlement $entitlement, $object): bool
     {
         $type = static::entitleableClass();
 
         if (empty($type) || empty($entitlement->entitleable_type)) {
             \Log::error("Entitleable class/type not specified");
             return false;
         }
 
         if ($type !== $entitlement->entitleable_type) {
             \Log::error("Entitleable class mismatch");
             return false;
         }
 
         if (!$entitlement->sku->active) {
             \Log::error("Sku not active");
             return false;
         }
 
         return true;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 0;
     }
 }
diff --git a/src/app/Handlers/Beta.php b/src/app/Handlers/Beta.php
index f54d3302..8dd10bd8 100644
--- a/src/app/Handlers/Beta.php
+++ b/src/app/Handlers/Beta.php
@@ -1,48 +1,41 @@
 <?php
 
 namespace App\Handlers;
 
+use App\Entitlement;
+
 class Beta extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
     /**
      * Prerequisites for the Entitlement to be applied to the object.
-     *
-     * @param \App\Entitlement $entitlement
-     * @param mixed $object
-     *
-     * @return bool
      */
-    public static function preReq($entitlement, $object): bool
+    public static function preReq(Entitlement $entitlement, $object): bool
     {
         // We allow inactive "beta" Sku to be assigned
 
         if (self::entitleableClass() !== $entitlement->entitleable_type) {
             \Log::error("Entitleable class mismatch");
             return false;
         }
 
         return true;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         // Just above all other beta SKUs, please
         return 10;
     }
 }
diff --git a/src/app/Handlers/Domain.php b/src/app/Handlers/Domain.php
index 7bb76797..0da84d36 100644
--- a/src/app/Handlers/Domain.php
+++ b/src/app/Handlers/Domain.php
@@ -1,16 +1,14 @@
 <?php
 
 namespace App\Handlers;
 
 class Domain extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Domain::class;
     }
 }
diff --git a/src/app/Handlers/DomainHosting.php b/src/app/Handlers/DomainHosting.php
index dfcb6fcd..0e6dcb68 100644
--- a/src/app/Handlers/DomainHosting.php
+++ b/src/app/Handlers/DomainHosting.php
@@ -1,33 +1,27 @@
 <?php
 
 namespace App\Handlers;
 
 class DomainHosting extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Domain::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['readonly'] = true;
         $data['enabled'] = true;
 
         return $data;
     }
 }
diff --git a/src/app/Handlers/DomainRegistration.php b/src/app/Handlers/DomainRegistration.php
index 77ad1fe5..43e3c57f 100644
--- a/src/app/Handlers/DomainRegistration.php
+++ b/src/app/Handlers/DomainRegistration.php
@@ -1,16 +1,14 @@
 <?php
 
 namespace App\Handlers;
 
 class DomainRegistration extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Domain::class;
     }
 }
diff --git a/src/app/Handlers/DomainRelay.php b/src/app/Handlers/DomainRelay.php
index d96fe7c8..9f31c150 100644
--- a/src/app/Handlers/DomainRelay.php
+++ b/src/app/Handlers/DomainRelay.php
@@ -1,16 +1,14 @@
 <?php
 
 namespace App\Handlers;
 
 class DomainRelay extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Domain::class;
     }
 }
diff --git a/src/app/Handlers/Group.php b/src/app/Handlers/Group.php
index 1af95f9a..267b5eb7 100644
--- a/src/app/Handlers/Group.php
+++ b/src/app/Handlers/Group.php
@@ -1,33 +1,27 @@
 <?php
 
 namespace App\Handlers;
 
 class Group extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Group::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['readonly'] = true;
         $data['enabled'] = true;
 
         return $data;
     }
 }
diff --git a/src/app/Handlers/GroupRoom.php b/src/app/Handlers/GroupRoom.php
index 9c68671b..1e415726 100644
--- a/src/app/Handlers/GroupRoom.php
+++ b/src/app/Handlers/GroupRoom.php
@@ -1,33 +1,27 @@
 <?php
 
 namespace App\Handlers;
 
 class GroupRoom extends Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Meet\Room::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['exclusive'] = ['Room'];
         $data['controllerOnly'] = true;
 
         return $data;
     }
 }
diff --git a/src/app/Handlers/Groupware.php b/src/app/Handlers/Groupware.php
index 26bf73c3..6f4ef7e4 100644
--- a/src/app/Handlers/Groupware.php
+++ b/src/app/Handlers/Groupware.php
@@ -1,27 +1,45 @@
 <?php
 
 namespace App\Handlers;
 
+use App\Entitlement;
+
 class Groupware extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
+    /**
+     * Handle entitlement creation event.
+     */
+    public static function entitlementCreated(Entitlement $entitlement): void
+    {
+        if (\config('app.with_ldap')) {
+            \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+        }
+    }
+
+    /**
+     * Handle entitlement deletion event.
+     */
+    public static function entitlementDeleted(Entitlement $entitlement): void
+    {
+        if (\config('app.with_ldap')) {
+            \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
+        }
+    }
+
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 80;
     }
 }
diff --git a/src/app/Handlers/Mailbox.php b/src/app/Handlers/Mailbox.php
index b28a1d88..35c88af5 100644
--- a/src/app/Handlers/Mailbox.php
+++ b/src/app/Handlers/Mailbox.php
@@ -1,45 +1,42 @@
 <?php
 
 namespace App\Handlers;
 
+use App\Entitlement;
+use App\Sku;
+
 class Mailbox extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
      *
      * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
-    public static function metadata(\App\Sku $sku): array
+    public static function metadata(Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         // Mailbox is always enabled and cannot be unset
         $data['readonly'] = true;
         $data['enabled'] = true;
 
         return $data;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 100;
     }
 }
diff --git a/src/app/Handlers/Resource.php b/src/app/Handlers/Resource.php
index bf4ffe6d..1b6a0a48 100644
--- a/src/app/Handlers/Resource.php
+++ b/src/app/Handlers/Resource.php
@@ -1,33 +1,27 @@
 <?php
 
 namespace App\Handlers;
 
 class Resource extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Resource::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['readonly'] = true;
         $data['enabled'] = true;
 
         return $data;
     }
 }
diff --git a/src/app/Handlers/Room.php b/src/app/Handlers/Room.php
index 1bd39945..96a7870e 100644
--- a/src/app/Handlers/Room.php
+++ b/src/app/Handlers/Room.php
@@ -1,44 +1,36 @@
 <?php
 
 namespace App\Handlers;
 
 class Room extends Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\Meet\Room::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['enabled'] = true;
         $data['exclusive'] = ['GroupRoom'];
 
         return $data;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 10;
     }
 }
diff --git a/src/app/Handlers/SharedFolder.php b/src/app/Handlers/SharedFolder.php
index 42af9dce..d0a6caf4 100644
--- a/src/app/Handlers/SharedFolder.php
+++ b/src/app/Handlers/SharedFolder.php
@@ -1,33 +1,27 @@
 <?php
 
 namespace App\Handlers;
 
 class SharedFolder extends \App\Handlers\Base
 {
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\SharedFolder::class;
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
     public static function metadata(\App\Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['readonly'] = true;
         $data['enabled'] = true;
 
         return $data;
     }
 }
diff --git a/src/app/Handlers/Storage.php b/src/app/Handlers/Storage.php
index 46f85897..b910f9fc 100644
--- a/src/app/Handlers/Storage.php
+++ b/src/app/Handlers/Storage.php
@@ -1,72 +1,65 @@
 <?php
 
 namespace App\Handlers;
 
 use App\Entitlement;
+use App\Sku;
 
 class Storage extends \App\Handlers\Base
 {
     public const MAX_ITEMS = 100;
     public const ITEM_UNIT = 'GB';
 
     /**
      * The entitleable class for this handler.
-     *
-     * @return string
      */
     public static function entitleableClass(): string
     {
         return \App\User::class;
     }
 
     /**
      * Handle entitlement creation event.
      */
     public static function entitlementCreated(Entitlement $entitlement): void
     {
         // Update the user IMAP mailbox quota
         \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
     }
 
     /**
      * Handle entitlement deletion event.
      */
     public static function entitlementDeleted(Entitlement $entitlement): void
     {
         // Update the user IMAP mailbox quota
         \App\Jobs\User\UpdateJob::dispatch($entitlement->entitleable_id);
     }
 
     /**
      * SKU handler metadata.
-     *
-     * @param \App\Sku $sku The SKU object
-     *
-     * @return array
      */
-    public static function metadata(\App\Sku $sku): array
+    public static function metadata(Sku $sku): array
     {
         $data = parent::metadata($sku);
 
         $data['readonly'] = true; // only the checkbox will be disabled, not range
         $data['enabled'] = true;
         $data['range'] = [
            'min' => $sku->units_free,
            'max' => self::MAX_ITEMS,
            'unit' => self::ITEM_UNIT,
         ];
 
         return $data;
     }
 
     /**
      * The priority that specifies the order of SKUs in UI.
      * Higher number means higher on the list.
-     *
-     * @return int
      */
     public static function priority(): int
     {
         return 90;
     }
 }
diff --git a/src/tests/Feature/EntitlementTest.php b/src/tests/Feature/EntitlementTest.php
index 4c04a455..ab195e3d 100644
--- a/src/tests/Feature/EntitlementTest.php
+++ b/src/tests/Feature/EntitlementTest.php
@@ -1,206 +1,245 @@
 <?php
 
 namespace Tests\Feature;
 
 use App\Domain;
 use App\Entitlement;
 use App\Package;
 use App\Sku;
 use App\User;
 use Carbon\Carbon;
 use Illuminate\Support\Facades\Queue;
 use Tests\TestCase;
 
 class EntitlementTest extends TestCase
 {
     /**
      * {@inheritDoc}
      */
     public function setUp(): void
     {
         parent::setUp();
 
         $this->deleteTestUser('entitlement-test@kolabnow.com');
         $this->deleteTestUser('entitled-user@custom-domain.com');
         $this->deleteTestGroup('test-group@custom-domain.com');
         $this->deleteTestDomain('custom-domain.com');
     }
 
     /**
      * {@inheritDoc}
      */
     public function tearDown(): void
     {
         $this->deleteTestUser('entitlement-test@kolabnow.com');
         $this->deleteTestUser('entitled-user@custom-domain.com');
         $this->deleteTestGroup('test-group@custom-domain.com');
         $this->deleteTestDomain('custom-domain.com');
 
         parent::tearDown();
     }
 
     /**
      * Tests for EntitlementObserver
-     *
-     * @group skipci
      */
     public function testEntitlementObserver(): void
     {
         $skuStorage = Sku::withEnvTenantContext()->where('title', 'storage')->first();
         $skuMailbox = Sku::withEnvTenantContext()->where('title', 'mailbox')->first();
+        $skuGroupware = Sku::withEnvTenantContext()->where('title', 'groupware')->first();
+        $skuActivesync = Sku::withEnvTenantContext()->where('title', 'activesync')->first();
+        $sku2FA = Sku::withEnvTenantContext()->where('title', '2fa')->first();
+        $skuBeta = Sku::withEnvTenantContext()->where('title', 'beta')->first();
         $user = $this->getTestUser('entitlement-test@kolabnow.com');
         $wallet = $user->wallets->first();
 
-        // Test dispatching update jobs for the user, on quota update
+        $assertPushedUserUpdateJob = function ($ifLdap = false) use ($user) {
+            if ($ifLdap && !\config('app.with_ldap')) {
+                Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
+                return;
+            }
+
+            Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 1);
+            Queue::assertPushed(
+                \App\Jobs\User\UpdateJob::class,
+                function ($job) use ($user) {
+                    return $user->id === TestCase::getObjectProperty($job, 'userId');
+                }
+            );
+        };
+
+        // Note: This also is testing SKU handlers
+
+        // 'mailbox' SKU should not dispatch update jobs
         $this->fakeQueueReset();
         $user->assignSku($skuMailbox, 1, $wallet);
         Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $skuMailbox->id)->first()->delete();
+        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
 
+        // Test dispatching update jobs for the user - 'storage' SKU
         $this->fakeQueueReset();
         $user->assignSku($skuStorage, 1, $wallet);
-        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 1);
-        Queue::assertPushed(
-            \App\Jobs\User\UpdateJob::class,
-            function ($job) use ($user) {
-                return $user->id === TestCase::getObjectProperty($job, 'userId');
-            }
-        );
+        $assertPushedUserUpdateJob();
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $skuStorage->id)->first()->delete();
+        $assertPushedUserUpdateJob();
 
+        // Test dispatching update jobs for the user - 'groupware' SKU
         $this->fakeQueueReset();
-        $user->entitlements()->where('sku_id', $skuMailbox->id)->first()->delete();
-        //FIXME this sometimes gives 1?
-        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
+        $user->assignSku($skuGroupware, 1, $wallet);
+        $assertPushedUserUpdateJob(true);
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $skuGroupware->id)->first()->delete();
+        $assertPushedUserUpdateJob(true);
 
+        // Test dispatching update jobs for the user - 'activesync' SKU
         $this->fakeQueueReset();
-        $user->entitlements()->where('sku_id', $skuStorage->id)->first()->delete();
-        //FIXME this sometimes gives 2?
-        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 1);
-        Queue::assertPushed(
-            \App\Jobs\User\UpdateJob::class,
-            function ($job) use ($user) {
-                return $user->id === TestCase::getObjectProperty($job, 'userId');
-            }
-        );
+        $user->assignSku($skuActivesync, 1, $wallet);
+        $assertPushedUserUpdateJob(true);
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $skuActivesync->id)->first()->delete();
+        $assertPushedUserUpdateJob(true);
+
+        // Test dispatching update jobs for the user - '2fa' SKU
+        $this->fakeQueueReset();
+        $user->assignSku($sku2FA, 1, $wallet);
+        $assertPushedUserUpdateJob(true);
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $sku2FA->id)->first()->delete();
+        $assertPushedUserUpdateJob(true);
+
+        // Beta SKU should not trigger a user update job
+        $this->fakeQueueReset();
+        $user->assignSku($skuBeta, 1, $wallet);
+        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
+        $this->fakeQueueReset();
+        $user->entitlements()->where('sku_id', $skuBeta->id)->first()->delete();
+        Queue::assertPushed(\App\Jobs\User\UpdateJob::class, 0);
 
-        // TODO: Test all events in the observer in more detail
+        // TODO: Assert 'creating' checks
+        // TODO: Assert transaction records being created
+        // TODO: Assert timestamps not updated on delete
+        $this->markTestIncomplete();
     }
 
     /**
      * Tests for entitlements
      * @todo This really should be in User or Wallet tests file
      */
     public function testEntitlements(): void
     {
         $packageDomain = Package::withEnvTenantContext()->where('title', 'domain-hosting')->first();
         $packageKolab = Package::withEnvTenantContext()->where('title', 'kolab')->first();
 
         $skuDomain = Sku::withEnvTenantContext()->where('title', 'domain-hosting')->first();
         $skuMailbox = Sku::withEnvTenantContext()->where('title', 'mailbox')->first();
 
         $owner = $this->getTestUser('entitlement-test@kolabnow.com');
         $user = $this->getTestUser('entitled-user@custom-domain.com');
 
         $domain = $this->getTestDomain(
             'custom-domain.com',
             [
                 'status' => Domain::STATUS_NEW,
                 'type' => Domain::TYPE_EXTERNAL,
             ]
         );
 
         $domain->assignPackage($packageDomain, $owner);
         $owner->assignPackage($packageKolab);
         $owner->assignPackage($packageKolab, $user);
 
         $wallet = $owner->wallets->first();
 
         $this->assertCount(7, $owner->entitlements()->get());
         $this->assertCount(1, $skuDomain->entitlements()->where('wallet_id', $wallet->id)->get());
         $this->assertCount(2, $skuMailbox->entitlements()->where('wallet_id', $wallet->id)->get());
         $this->assertCount(15, $wallet->entitlements);
 
         $this->backdateEntitlements(
             $owner->entitlements,
             Carbon::now()->subMonthsWithoutOverflow(1)
         );
 
         $wallet->chargeEntitlements();
 
         $this->assertTrue($wallet->fresh()->balance < 0);
     }
 
     /**
      * Test EntitleableTrait::toString()
      */
     public function testEntitleableTitle(): void
     {
         $packageDomain = Package::withEnvTenantContext()->where('title', 'domain-hosting')->first();
         $packageKolab = Package::withEnvTenantContext()->where('title', 'kolab')->first();
         $user = $this->getTestUser('entitled-user@custom-domain.com');
         $group = $this->getTestGroup('test-group@custom-domain.com');
 
         $domain = $this->getTestDomain(
             'custom-domain.com',
             [
                 'status' => Domain::STATUS_NEW,
                 'type' => Domain::TYPE_EXTERNAL,
             ]
         );
 
         $wallet = $user->wallets->first();
         $domain->assignPackage($packageDomain, $user);
         $user->assignPackage($packageKolab);
         $group->assignToWallet($wallet);
 
         $sku_mailbox = \App\Sku::withEnvTenantContext()->where('title', 'mailbox')->first();
         $sku_group = \App\Sku::withEnvTenantContext()->where('title', 'group')->first();
         $sku_domain = \App\Sku::withEnvTenantContext()->where('title', 'domain-hosting')->first();
 
         $entitlement = Entitlement::where('wallet_id', $wallet->id)
             ->where('sku_id', $sku_mailbox->id)->first();
 
         $this->assertSame($user->email, $entitlement->entitleable->toString());
 
         $entitlement = Entitlement::where('wallet_id', $wallet->id)
             ->where('sku_id', $sku_group->id)->first();
 
         $this->assertSame($group->email, $entitlement->entitleable->toString());
 
         $entitlement = Entitlement::where('wallet_id', $wallet->id)
             ->where('sku_id', $sku_domain->id)->first();
 
         $this->assertSame($domain->namespace, $entitlement->entitleable->toString());
 
         // Make sure it still works if the entitleable is deleted
         $domain->delete();
 
         $entitlement->refresh();
 
         $this->assertSame($domain->namespace, $entitlement->entitleable->toString());
         $this->assertNotNull($entitlement->entitleable);
     }
 
     /**
      * Test for EntitleableTrait::removeSku()
      */
     public function testEntitleableRemoveSku(): void
     {
         $user = $this->getTestUser('entitlement-test@kolabnow.com');
         $storage = \App\Sku::withEnvTenantContext()->where('title', 'storage')->first();
 
         $user->assignSku($storage, 6);
 
         $this->assertCount(6, $user->fresh()->entitlements);
 
         $backdate = Carbon::now()->subWeeks(7);
         $this->backdateEntitlements($user->entitlements, $backdate);
 
         $user->removeSku($storage, 2);
 
         // Expect free units to be not deleted
         $this->assertCount(5, $user->fresh()->entitlements);
 
         // Here we make sure that updated_at does not change on delete
         $this->assertSame(6, $user->entitlements()->withTrashed()->whereDate('updated_at', $backdate)->count());
     }
 }