diff --git a/src/StarfaceOutlookSync/Services/SyncEngine.cs b/src/StarfaceOutlookSync/Services/SyncEngine.cs
index 3b4057f5..cb96917c 100644
--- a/src/StarfaceOutlookSync/Services/SyncEngine.cs
+++ b/src/StarfaceOutlookSync/Services/SyncEngine.cs
@@ -144,6 +144,45 @@ namespace StarfaceOutlookSync.Services
                         if (oc == null && sc == null)
                         {
                             // Beide Seiten geloescht -> Mapping entfernen
+                            Log($"  Mapping verwaist (beide geloescht), entferne");
+                            continue;
+                        }
+
+                        if (oc == null && sc != null)
+                        {
+                            // In Outlook geloescht -> in Starface auch loeschen
+                            if (profile.SyncDirection == SyncDirection.Both || profile.SyncDirection == SyncDirection.OutlookToStarface)
+                            {
+                                if (await starface.DeleteContactAsync(mapping.StarfaceId))
+                                {
+                                    result.Updated++;
+                                    Log($"  Geloescht (OL->SF): {sc.DisplayName}");
+                                }
+                            }
+                            else
+                            {
+                                // Richtung erlaubt kein Loeschen -> Mapping behalten
+                                newMappings.Add(mapping);
+                            }
+                            continue;
+                        }
+
+                        if (oc != null && sc == null)
+                        {
+                            // In Starface geloescht -> in Outlook auch loeschen
+                            if (profile.SyncDirection == SyncDirection.Both || profile.SyncDirection == SyncDirection.StarfaceToOutlook)
+                            {
+                                if (_outlookService.DeleteContact(mapping.OutlookEntryId))
+                                {
+                                    result.Updated++;
+                                    Log($"  Geloescht (SF->OL): {oc.DisplayName}");
+                                }
+                            }
+                            else
+                            {
+                                // Richtung erlaubt kein Loeschen -> Mapping behalten
+                                newMappings.Add(mapping);
+                            }
                             continue;
                         }