diff --git a/app/Console/Commands/SyncChurchToolsCommand.php b/app/Console/Commands/SyncChurchToolsCommand.php
index c1dde2e..5fdd4e8 100644
--- a/app/Console/Commands/SyncChurchToolsCommand.php
+++ b/app/Console/Commands/SyncChurchToolsCommand.php
@@ -3,6 +3,9 @@
 namespace App\Console\Commands;
 
 use App\Services\ChurchToolsService;
+use CTApi\Exceptions\CTConnectException;
+use CTApi\Exceptions\CTPermissionException;
+use CTApi\Exceptions\CTRequestException;
 use Illuminate\Console\Command;
 use Throwable;
 
@@ -24,8 +27,44 @@ public function handle(ChurchToolsService $churchToolsService): int
             $this->line('Nicht gematchte Songs: '.$summary['unmatched_songs_count']);
 
             return self::SUCCESS;
-        } catch (Throwable $exception) {
-            $this->error('Fehler beim Synchronisieren: '.$exception->getMessage());
+        } catch (CTPermissionException $e) {
+            $this->error('Authentifizierungsfehler: API-Token ungueltig oder abgelaufen.');
+            $this->error('Bitte pruefe CTS_API_TOKEN in der .env Datei.');
+            $this->line('  Details: '.$e->getMessage());
+
+            if ($this->getOutput()->isVerbose()) {
+                $this->line('  Exception: '.$e::class);
+                $this->line('  Trace: '.$e->getTraceAsString());
+            }
+
+            return self::FAILURE;
+        } catch (CTConnectException $e) {
+            $this->error('Verbindungsfehler: ChurchTools Server nicht erreichbar.');
+            $this->error('Bitte pruefe CTS_API_URL in der .env Datei und die Netzwerkverbindung.');
+            $this->line('  Details: '.$e->getMessage());
+
+            if ($this->getOutput()->isVerbose()) {
+                $this->line('  Exception: '.$e::class);
+                $this->line('  Trace: '.$e->getTraceAsString());
+            }
+
+            return self::FAILURE;
+        } catch (CTRequestException $e) {
+            $this->error('API-Fehler: '.$e->getMessage());
+            $this->line('  Exception: '.$e::class);
+
+            if ($this->getOutput()->isVerbose()) {
+                $this->line('  Trace: '.$e->getTraceAsString());
+            }
+
+            return self::FAILURE;
+        } catch (Throwable $e) {
+            $this->error('Fehler beim Synchronisieren: '.$e->getMessage());
+            $this->line('  Exception: '.$e::class);
+
+            if ($this->getOutput()->isVerbose()) {
+                $this->line('  Trace: '.$e->getTraceAsString());
+            }
 
             return self::FAILURE;
         }
diff --git a/app/Http/Controllers/SyncController.php b/app/Http/Controllers/SyncController.php
index 317ca8a..2caa652 100644
--- a/app/Http/Controllers/SyncController.php
+++ b/app/Http/Controllers/SyncController.php
@@ -3,7 +3,10 @@
 namespace App\Http\Controllers;
 
 use App\Services\ChurchToolsService;
+use CTApi\Exceptions\CTConnectException;
+use CTApi\Exceptions\CTPermissionException;
 use Illuminate\Http\RedirectResponse;
+use Illuminate\Support\Facades\Log;
 
 class SyncController extends Controller
 {
@@ -13,7 +16,26 @@ public function sync(ChurchToolsService $service): RedirectResponse
             $service->sync();
 
             return back()->with('success', 'Daten wurden aktualisiert');
+        } catch (CTPermissionException $e) {
+            Log::error('CTS Sync: Authentifizierungsfehler', [
+                'nachricht' => $e->getMessage(),
+                'exception_klasse' => $e::class,
+            ]);
+
+            return back()->with('error', 'Sync fehlgeschlagen: Authentifizierung abgelehnt. Bitte prüfe den API-Token in der .env Datei.');
+        } catch (CTConnectException $e) {
+            Log::error('CTS Sync: Verbindungsfehler', [
+                'nachricht' => $e->getMessage(),
+                'exception_klasse' => $e::class,
+            ]);
+
+            return back()->with('error', 'Sync fehlgeschlagen: Verbindung zu ChurchTools nicht möglich. Bitte prüfe die URL und Netzwerkverbindung.');
         } catch (\Throwable $e) {
+            Log::error('CTS Sync: Unerwarteter Fehler', [
+                'nachricht' => $e->getMessage(),
+                'exception_klasse' => $e::class,
+            ]);
+
             return back()->with('error', 'Sync fehlgeschlagen: '.$e->getMessage());
         }
     }