diff --git a/custom/Espo/Custom/Hooks/CAkten/UpdateLastSyncFromDocuments.php b/custom/Espo/Custom/Hooks/CAkten/UpdateLastSyncFromDocuments.php
index e6410835..a3d1c64d 100644
--- a/custom/Espo/Custom/Hooks/CAkten/UpdateLastSyncFromDocuments.php
+++ b/custom/Espo/Custom/Hooks/CAkten/UpdateLastSyncFromDocuments.php
@@ -6,8 +6,8 @@ use Espo\ORM\Repository\Option\SaveOptions;
 use Espo\Core\Hook\Hook\BeforeSave;
 
 /**
- * Hook: Aktualisiert lastSync basierend auf dem neuesten lastSyncTimestamp
- * der verknüpften Dokumente
+ * Hook: Aktualisiert lastSync + syncStatus (Advoware) und aiLastSync + aiSyncStatus (AI)
+ * basierend auf dem neuesten Timestamp und schlechtesten Status der verknüpften Dokumente.
  */
 class UpdateLastSyncFromDocuments implements BeforeSave
 {
@@ -17,12 +17,10 @@ class UpdateLastSyncFromDocuments implements BeforeSave
 
     public function beforeSave(Entity $entity, SaveOptions $options): void
     {
-        // Überspringe, wenn skipHooks gesetzt ist (verhindert Loops)
         if ($options->get('skipHooks')) {
             return;
         }
 
-        // Nur wenn Entity bereits existiert (nicht bei Create)
         if ($entity->isNew()) {
             return;
         }
@@ -31,62 +29,96 @@ class UpdateLastSyncFromDocuments implements BeforeSave
             $pdo = $this->entityManager->getPDO();
             $aktenId = $entity->getId();
 
-            // Hole das neueste lastSyncTimestamp aller verknüpften Dokumente
             $stmt = $pdo->prepare(
-                "SELECT MAX(last_sync_timestamp) AS maxLastSync
+                "SELECT
+                     MAX(last_sync_timestamp) AS maxAdvLastSync,
+                     MAX(ai_last_sync)       AS maxAiLastSync,
+                     sync_status,
+                     ai_sync_status
                  FROM c_dokumente
-                 WHERE c_akten_id = :aktenId AND deleted = 0 AND last_sync_timestamp IS NOT NULL"
+                 WHERE c_akten_id = :aktenId AND deleted = 0"
             );
             $stmt->execute([':aktenId' => $aktenId]);
-            $result = $stmt->fetch(\PDO::FETCH_ASSOC);
+            $rows = $stmt->fetchAll(\PDO::FETCH_ASSOC);
 
-            if ($result && $result['maxLastSync']) {
-                $entity->set('lastSync', $result['maxLastSync']);
+            if (empty($rows)) {
+                $entity->set('syncStatus', 'unclean');
+                $entity->set('aiSyncStatus', 'unclean');
+                return;
             }
 
-            // Berechne syncStatus basierend auf verknüpften Dokumenten
-            $this->updateSyncStatus($entity, $pdo, $aktenId);
+            // Timestamps
+            $maxAdvLastSync = null;
+            $maxAiLastSync  = null;
+
+            // Status-Tracker
+            $advHasFailed   = false;
+            $advHasUnsynced = false;
+            $aiHasFailed    = false;
+            $aiHasUnsynced  = false;
+
+            foreach ($rows as $row) {
+                // Advoware: neuester Timestamp
+                if (!empty($row['maxAdvLastSync'])) {
+                    if ($maxAdvLastSync === null || $row['maxAdvLastSync'] > $maxAdvLastSync) {
+                        $maxAdvLastSync = $row['maxAdvLastSync'];
+                    }
+                }
+
+                // AI: neuester Timestamp
+                if (!empty($row['maxAiLastSync'])) {
+                    if ($maxAiLastSync === null || $row['maxAiLastSync'] > $maxAiLastSync) {
+                        $maxAiLastSync = $row['maxAiLastSync'];
+                    }
+                }
+
+                // Advoware: schlechtester Status
+                $advStatus = $row['sync_status'] ?? null;
+                if ($advStatus === 'failed') {
+                    $advHasFailed = true;
+                } elseif ($advStatus === 'new' || $advStatus === 'unclean' || $advStatus === null || $advStatus === '') {
+                    $advHasUnsynced = true;
+                }
+
+                // AI: schlechtester Status
+                $aiStatus = $row['ai_sync_status'] ?? null;
+                if ($aiStatus === 'failed') {
+                    $aiHasFailed = true;
+                } elseif ($aiStatus === 'new' || $aiStatus === 'unclean' || $aiStatus === null || $aiStatus === '') {
+                    $aiHasUnsynced = true;
+                }
+            }
+
+            // Advoware Timestamp setzen
+            if ($maxAdvLastSync !== null) {
+                $entity->set('lastSync', $maxAdvLastSync);
+            }
+
+            // AI Timestamp setzen
+            if ($maxAiLastSync !== null) {
+                $entity->set('aiLastSync', $maxAiLastSync);
+            }
+
+            // Advoware Status setzen (worst-case)
+            if ($advHasFailed) {
+                $entity->set('syncStatus', 'failed');
+            } elseif ($advHasUnsynced) {
+                $entity->set('syncStatus', 'unclean');
+            } else {
+                $entity->set('syncStatus', 'synced');
+            }
+
+            // AI Status setzen (worst-case)
+            if ($aiHasFailed) {
+                $entity->set('aiSyncStatus', 'failed');
+            } elseif ($aiHasUnsynced) {
+                $entity->set('aiSyncStatus', 'unclean');
+            } else {
+                $entity->set('aiSyncStatus', 'synced');
+            }
 
         } catch (\Exception $e) {
             $GLOBALS['log']->error('CAkten UpdateLastSyncFromDocuments Hook Error: ' . $e->getMessage());
         }
     }
-
-    private function updateSyncStatus(Entity $entity, \PDO $pdo, string $aktenId): void
-    {
-        $stmt = $pdo->prepare(
-            "SELECT sync_status FROM c_dokumente
-             WHERE c_akten_id = :aktenId AND deleted = 0"
-        );
-        $stmt->execute([':aktenId' => $aktenId]);
-        $rows = $stmt->fetchAll(\PDO::FETCH_ASSOC);
-
-        if (empty($rows)) {
-            $entity->set('syncStatus', 'unclean');
-            return;
-        }
-
-        $hasUnsynced = false;
-        $hasFailed = false;
-
-        foreach ($rows as $row) {
-            $status = $row['sync_status'] ?? null;
-
-            if ($status === 'failed') {
-                $hasFailed = true;
-            }
-
-            if ($status === 'new' || $status === 'unclean' || $status === null || $status === '') {
-                $hasUnsynced = true;
-            }
-        }
-
-        if ($hasFailed) {
-            $entity->set('syncStatus', 'failed');
-        } elseif ($hasUnsynced) {
-            $entity->set('syncStatus', 'unclean');
-        } else {
-            $entity->set('syncStatus', 'synced');
-        }
-    }
 }
diff --git a/data/state.php b/data/state.php
index 2003120b..fecbe14e 100644
--- a/data/state.php
+++ b/data/state.php
@@ -1,7 +1,7 @@
 <?php
 return [
-  'cacheTimestamp' => 1774530224,
-  'microtimeState' => 1774530224.017606,
+  'cacheTimestamp' => 1774530556,
+  'microtimeState' => 1774530556.202809,
   'currencyRates' => [
     'EUR' => 1.0
   ],