diff --git a/lib/src/services/api.service.dart b/lib/src/services/api.service.dart
index c81d224d..623db097 100644
--- a/lib/src/services/api.service.dart
+++ b/lib/src/services/api.service.dart
@@ -90,6 +90,11 @@ class ApiService {
   StreamSubscription<List<ConnectivityResult>>? _connectivitySubscription;
 
   Future<bool> _connectTo(String apiUrl) async {
+    if (kDebugMode) {
+      print(
+        'DEBUG: ApiService._connectTo called with: $apiUrl (appIsOutdated=$appIsOutdated)',
+      );
+    }
     if (appIsOutdated) return false;
     try {
       final channel = IOWebSocketChannel.connect(
@@ -101,7 +106,10 @@ class ApiService {
       await _channel!.ready;
       Log.info('websocket connected to $apiUrl');
       return true;
-    } catch (_) {
+    } catch (e, s) {
+      if (kDebugMode) {
+        print('DEBUG: _connectTo caught exception: $e\n$s');
+      }
       return false;
     }
   }
diff --git a/lib/src/services/api/client2client/additional_data.c2c.dart b/lib/src/services/api/client2client/additional_data.c2c.dart
index 5a451bb4..e99747db 100644
--- a/lib/src/services/api/client2client/additional_data.c2c.dart
+++ b/lib/src/services/api/client2client/additional_data.c2c.dart
@@ -10,9 +10,10 @@ Future<void> handleAdditionalDataMessage(
   int fromUserId,
   String groupId,
   EncryptedContent_AdditionalDataMessage message,
+  String receiptId,
 ) async {
   Log.info(
-    'Got a additional data message: ${message.senderMessageId} from $groupId',
+    '[$receiptId] Got a additional data message: ${message.senderMessageId} from $groupId',
   );
 
   // Prevent message overwrite: reject if a message with this ID already
@@ -22,7 +23,7 @@ Future<void> handleAdditionalDataMessage(
       .getSingleOrNull();
   if (existing != null && existing.senderId != fromUserId) {
     Log.warn(
-      '$fromUserId tried to overwrite message from ${existing.senderId}. Dropping.',
+      '[$receiptId] $fromUserId tried to overwrite message from ${existing.senderId}. Dropping.',
     );
     return;
   }
@@ -45,6 +46,6 @@ Future<void> handleAdditionalDataMessage(
     fromTimestamp(message.timestamp),
   );
   if (msg != null) {
-    Log.info('Inserted a new text message with ID: ${msg.messageId}');
+    Log.info('[$receiptId] Inserted a new text message with ID: ${msg.messageId}');
   }
 }
diff --git a/lib/src/services/api/client2client/contact.c2c.dart b/lib/src/services/api/client2client/contact.c2c.dart
index af306db3..8077d76f 100644
--- a/lib/src/services/api/client2client/contact.c2c.dart
+++ b/lib/src/services/api/client2client/contact.c2c.dart
@@ -88,16 +88,17 @@ Future<void> handleContactAccept(int fromUserId) async {
 Future<bool> handleContactRequest(
   int fromUserId,
   EncryptedContent_ContactRequest contactRequest,
+  String receiptId,
 ) async {
   switch (contactRequest.type) {
     case EncryptedContent_ContactRequest_Type.REQUEST:
-      Log.info('Got a contact request from $fromUserId');
+      Log.info('[$receiptId] Got a contact request from $fromUserId');
       return handleNewContactRequest(fromUserId);
     case EncryptedContent_ContactRequest_Type.ACCEPT:
-      Log.info('Got a contact accept from $fromUserId');
+      Log.info('[$receiptId] Got a contact accept from $fromUserId');
       await handleContactAccept(fromUserId);
     case EncryptedContent_ContactRequest_Type.REJECT:
-      Log.info('Got a contact reject from $fromUserId');
+      Log.info('[$receiptId] Got a contact reject from $fromUserId');
       await twonlyDB.contactsDao.updateContact(
         fromUserId,
         const ContactsCompanion(
@@ -114,14 +115,15 @@ Future<void> handleContactUpdate(
   int fromUserId,
   EncryptedContent_ContactUpdate contactUpdate,
   int? senderProfileCounter,
+  String receiptId,
 ) async {
   switch (contactUpdate.type) {
     case EncryptedContent_ContactUpdate_Type.REQUEST:
-      Log.info('Got a contact update request from $fromUserId');
+      Log.info('[$receiptId] Got a contact update request from $fromUserId');
       await sendContactMyProfileData(fromUserId);
 
     case EncryptedContent_ContactUpdate_Type.UPDATE:
-      Log.info('Got a contact update $fromUserId');
+      Log.info('[$receiptId] Got a contact update $fromUserId');
       Uint8List? avatarSvgCompressed;
       if (contactUpdate.hasAvatarSvgCompressed()) {
         avatarSvgCompressed = Uint8List.fromList(
@@ -188,8 +190,9 @@ Future<void> handleContactUpdate(
 Future<void> handleFlameSync(
   String groupId,
   EncryptedContent_FlameSync flameSync,
+  String receiptId,
 ) async {
-  Log.info('Got a flameSync for group $groupId');
+  Log.info('[$receiptId] Got a flameSync for group $groupId');
 
   final group = await twonlyDB.groupsDao.getGroup(groupId);
   if (group == null || group.lastFlameCounterChange == null) return;
diff --git a/lib/src/services/api/client2client/errors.c2c.dart b/lib/src/services/api/client2client/errors.c2c.dart
index bc03adfd..6aa093a2 100644
--- a/lib/src/services/api/client2client/errors.c2c.dart
+++ b/lib/src/services/api/client2client/errors.c2c.dart
@@ -8,8 +8,9 @@ import 'package:twonly/src/utils/log.dart';
 Future<void> handleErrorMessage(
   int fromUserId,
   EncryptedContent_ErrorMessages error,
+  String receiptId,
 ) async {
-  Log.error('Got error from $fromUserId: $error');
+  Log.error('[$receiptId] Got error from $fromUserId: $error');
 
   switch (error.type) {
     case EncryptedContent_ErrorMessages_Type
diff --git a/lib/src/services/api/client2client/groups.c2c.dart b/lib/src/services/api/client2client/groups.c2c.dart
index f9fb9a1e..65876ff9 100644
--- a/lib/src/services/api/client2client/groups.c2c.dart
+++ b/lib/src/services/api/client2client/groups.c2c.dart
@@ -15,6 +15,7 @@ Future<void> handleGroupCreate(
   int fromUserId,
   String groupId,
   EncryptedContent_GroupCreate newGroup,
+  String receiptId,
 ) async {
   final user = await twonlyDB.contactsDao
       .getContactByUserId(fromUserId)
@@ -22,7 +23,7 @@ Future<void> handleGroupCreate(
   if (user == null) {
     // Only contacts can invite other contacts, so this can (via the UI) not happen.
     Log.error(
-      'User is not a contact. Aborting.',
+      '[$receiptId] User is not a contact. Aborting.',
     );
     return;
   }
@@ -66,7 +67,7 @@ Future<void> handleGroupCreate(
 
   if (group == null) {
     Log.error(
-      'Could not create new group. Probably because the group already existed.',
+      '[$receiptId] Could not create new group. Probably because the group already existed.',
     );
     return;
   }
@@ -108,12 +109,13 @@ Future<void> handleGroupUpdate(
   int fromUserId,
   String groupId,
   EncryptedContent_GroupUpdate update,
+  String receiptId,
 ) async {
-  Log.info('Got group update for $groupId from $fromUserId');
+  Log.info('[$receiptId] Got group update for $groupId from $fromUserId');
 
   final actionType = groupActionTypeFromString(update.groupActionType);
   if (actionType == null) {
-    Log.error('Group action ${update.groupActionType} is unknown ignoring.');
+    Log.error('[$receiptId] Group action ${update.groupActionType} is unknown ignoring.');
     return;
   }
 
@@ -189,10 +191,11 @@ Future<bool> handleGroupJoin(
   int fromUserId,
   String groupId,
   EncryptedContent_GroupJoin join,
+  String receiptId,
 ) async {
   if (await twonlyDB.contactsDao.getContactById(fromUserId) == null) {
     if (!await addNewHiddenContact(fromUserId)) {
-      Log.error('Got group join, but could not load contact.');
+      Log.error('[$receiptId] Got group join, but could not load contact.');
       // This can happen in case the group join was received before the group create.
       // In this case return false, which will cause the receipt to fail and the user
       // will resend this message.
@@ -213,6 +216,7 @@ Future<void> handleResendGroupPublicKey(
   int fromUserId,
   String groupId,
   EncryptedContent_GroupJoin join,
+  String receiptId,
 ) async {
   final group = await twonlyDB.groupsDao.getGroup(groupId);
   if (group == null || group.myGroupPrivateKey == null) return;
@@ -232,6 +236,7 @@ Future<void> handleTypingIndicator(
   int fromUserId,
   String groupId,
   EncryptedContent_TypingIndicator indicator,
+  String receiptId,
 ) async {
   var lastTypeIndicator = const Value<DateTime?>.absent();
 
diff --git a/lib/src/services/api/client2client/media.c2c.dart b/lib/src/services/api/client2client/media.c2c.dart
index 303cd3e2..ca282a71 100644
--- a/lib/src/services/api/client2client/media.c2c.dart
+++ b/lib/src/services/api/client2client/media.c2c.dart
@@ -18,9 +18,10 @@ Future<void> handleMedia(
   int fromUserId,
   String groupId,
   EncryptedContent_Media media,
+  String receiptId,
 ) async {
   Log.info(
-    'Got a media message: ${media.senderMessageId} from $groupId with type ${media.type}',
+    '[$receiptId] Got a media message: ${media.senderMessageId} from $groupId with type ${media.type}',
   );
 
   late MediaType mediaType;
@@ -33,7 +34,7 @@ Future<void> handleMedia(
           message.senderId != fromUserId ||
           message.mediaId == null) {
         Log.warn(
-          'Got reupload from $fromUserId for a message that either does not exists (${message == null}) or senderId = ${message?.senderId}',
+          '[$receiptId] Got reupload for a message that either does not exists (${message == null}) or senderId = ${message?.senderId}',
         );
         return;
       }
@@ -82,13 +83,13 @@ Future<void> handleMedia(
   if (messageTmp != null) {
     if (messageTmp.senderId != fromUserId) {
       Log.warn(
-        '$fromUserId tried to modify the message from ${messageTmp.senderId}.',
+        '[$receiptId] $fromUserId tried to modify the message from ${messageTmp.senderId}.',
       );
       return;
     }
     if (messageTmp.mediaId == null) {
       Log.warn(
-        'This message already exit without a mediaId. Message is dropped.',
+        '[$receiptId] This message already exit without a mediaId. Message is dropped.',
       );
       return;
     }
@@ -97,7 +98,7 @@ Future<void> handleMedia(
     );
     if (mediaFile?.downloadState != DownloadState.reuploadRequested) {
       Log.warn(
-        'This message and media file already exit and was not requested again. Dropping it.',
+        '[$receiptId] This message and media file already exit and was not requested again. Dropping it.',
       );
       return;
     }
@@ -121,7 +122,9 @@ Future<void> handleMedia(
   MediaFile? mediaFile;
   Message? message;
 
-  Log.info('Starting transaction for media message ${media.senderMessageId}');
+  Log.info(
+    '[$receiptId] Starting transaction for media message ${media.senderMessageId}',
+  );
   await twonlyDB.transaction(() async {
     mediaFile = await twonlyDB.mediaFilesDao.insertOrUpdateMedia(
       MediaFilesCompanion(
@@ -141,7 +144,7 @@ Future<void> handleMedia(
     );
 
     if (mediaFile == null) {
-      Log.error('Could not insert media file into database');
+      Log.error('[$receiptId] Could not insert media file into database');
       return;
     }
 
@@ -165,7 +168,7 @@ Future<void> handleMedia(
     );
   });
   Log.info(
-    'Finished transaction for media message ${media.senderMessageId}. Success: ${message != null}',
+    '[$receiptId] Finished transaction for media message ${media.senderMessageId}. Success: ${message != null}',
   );
 
   if (message != null && mediaFile != null) {
@@ -173,7 +176,9 @@ Future<void> handleMedia(
       groupId,
       fromTimestamp(media.timestamp),
     );
-    Log.info('Inserted a new media message with ID: ${message!.messageId}');
+    Log.info(
+      '[$receiptId] Inserted a new media message with ID: ${message!.messageId}',
+    );
     await incFlameCounter(
       message!.groupId,
       true,
@@ -184,12 +189,16 @@ Future<void> handleMedia(
   } else {
     if (mediaFile == null && message == null) {
       Log.error(
-        'Could not insert new message as both the message and mediaFile are empty.',
+        '[$receiptId] Could not insert new message as both the message and mediaFile are empty.',
       );
     } else if (mediaFile == null) {
-      Log.error('Could not insert new message as the mediaFile is empty.');
+      Log.error(
+        '[$receiptId] Could not insert new message as the mediaFile is empty.',
+      );
     } else {
-      Log.error('Could not insert new message as the message is empty.');
+      Log.error(
+        '[$receiptId] Could not insert new message as the message is empty.',
+      );
     }
   }
 }
@@ -197,6 +206,7 @@ Future<void> handleMedia(
 Future<void> handleMediaUpdate(
   int fromUserId,
   EncryptedContent_MediaUpdate mediaUpdate,
+  String receiptId,
 ) async {
   final message = await twonlyDB.messagesDao
       .getMessageById(mediaUpdate.targetMessageId)
@@ -204,14 +214,14 @@ Future<void> handleMediaUpdate(
   if (message == null) {
     // this can happen, in case the message was already deleted.
     Log.info(
-      'Got media update to message ${mediaUpdate.targetMessageId} but message not found.',
+      '[$receiptId] Got media update to message ${mediaUpdate.targetMessageId} but message not found.',
     );
     return;
   }
   if (message.mediaId == null) {
     // this can happen, in case the message was already deleted.
     Log.warn(
-      'Got media update for message ${mediaUpdate.targetMessageId} which does not have a mediaId defined.',
+      '[$receiptId] Got media update for message ${mediaUpdate.targetMessageId} which does not have a mediaId defined.',
     );
     return;
   }
@@ -220,14 +230,14 @@ Future<void> handleMediaUpdate(
   );
   if (mediaFile == null) {
     Log.info(
-      'Got media file update, but media file was not found ${message.mediaId}',
+      '[$receiptId] Got media file update, but media file was not found ${message.mediaId}',
     );
     return;
   }
 
   switch (mediaUpdate.type) {
     case EncryptedContent_MediaUpdate_Type.REOPENED:
-      Log.info('Got media file reopened ${mediaFile.mediaId}');
+      Log.info('[$receiptId] Got media file reopened ${mediaFile.mediaId}');
       await twonlyDB.messagesDao.updateMessageId(
         message.messageId,
         const MessagesCompanion(
@@ -235,7 +245,7 @@ Future<void> handleMediaUpdate(
         ),
       );
     case EncryptedContent_MediaUpdate_Type.STORED:
-      Log.info('Got media file stored ${mediaFile.mediaId}');
+      Log.info('[$receiptId] Got media file stored ${mediaFile.mediaId}');
       final mediaService = MediaFileService(mediaFile);
       await mediaService.storeMediaFile();
       await twonlyDB.messagesDao.updateMessageId(
@@ -246,7 +256,9 @@ Future<void> handleMediaUpdate(
       );
 
     case EncryptedContent_MediaUpdate_Type.DECRYPTION_ERROR:
-      Log.info('Got media file decryption error ${mediaFile.mediaId}');
+      Log.info(
+        '[$receiptId] Got media file decryption error ${mediaFile.mediaId}',
+      );
       await reuploadMediaFile(fromUserId, mediaFile, message.messageId);
   }
 }
diff --git a/lib/src/services/api/client2client/messages.c2c.dart b/lib/src/services/api/client2client/messages.c2c.dart
index 4561687f..a8f911fd 100644
--- a/lib/src/services/api/client2client/messages.c2c.dart
+++ b/lib/src/services/api/client2client/messages.c2c.dart
@@ -7,11 +7,12 @@ import 'package:twonly/src/utils/log.dart';
 Future<void> handleMessageUpdate(
   int contactId,
   EncryptedContent_MessageUpdate messageUpdate,
+  String receiptId,
 ) async {
   switch (messageUpdate.type) {
     case EncryptedContent_MessageUpdate_Type.OPENED:
       Log.info(
-        'Opened message ${messageUpdate.multipleTargetMessageIds}',
+        '[$receiptId] Opened message ${messageUpdate.multipleTargetMessageIds}',
       );
       try {
         await twonlyDB.messagesDao.handleMessagesOpened(
@@ -20,13 +21,13 @@ Future<void> handleMessageUpdate(
           fromTimestamp(messageUpdate.timestamp),
         );
       } catch (e) {
-        Log.warn(e);
+        Log.warn('[$receiptId] Error handling messages opened: $e');
       }
     case EncryptedContent_MessageUpdate_Type.DELETE:
-      if (!await isSender(contactId, messageUpdate.senderMessageId)) {
+      if (!await isSender(contactId, messageUpdate.senderMessageId, receiptId)) {
         return;
       }
-      Log.info('Delete message ${messageUpdate.senderMessageId}');
+      Log.info('[$receiptId] Delete message ${messageUpdate.senderMessageId}');
       try {
         await twonlyDB.messagesDao.handleMessageDeletion(
           contactId,
@@ -34,13 +35,13 @@ Future<void> handleMessageUpdate(
           fromTimestamp(messageUpdate.timestamp),
         );
       } catch (e) {
-        Log.warn(e);
+        Log.warn('[$receiptId] Error handling message deletion: $e');
       }
     case EncryptedContent_MessageUpdate_Type.EDIT_TEXT:
-      if (!await isSender(contactId, messageUpdate.senderMessageId)) {
+      if (!await isSender(contactId, messageUpdate.senderMessageId, receiptId)) {
         return;
       }
-      Log.info('Edit message ${messageUpdate.senderMessageId}');
+      Log.info('[$receiptId] Edit message ${messageUpdate.senderMessageId}');
       try {
         await twonlyDB.messagesDao.handleTextEdit(
           contactId,
@@ -49,12 +50,12 @@ Future<void> handleMessageUpdate(
           fromTimestamp(messageUpdate.timestamp),
         );
       } catch (e) {
-        Log.warn(e);
+        Log.warn('[$receiptId] Error handling text edit: $e');
       }
   }
 }
 
-Future<bool> isSender(int fromUserId, String messageId) async {
+Future<bool> isSender(int fromUserId, String messageId, String receiptId) async {
   final message = await twonlyDB.messagesDao
       .getMessageById(messageId)
       .getSingleOrNull();
@@ -62,6 +63,6 @@ Future<bool> isSender(int fromUserId, String messageId) async {
   if (message.senderId == fromUserId) {
     return true;
   }
-  Log.error('Contact $fromUserId tried to modify the message $messageId');
+  Log.error('[$receiptId] Contact $fromUserId tried to modify the message $messageId');
   return false;
 }
diff --git a/lib/src/services/api/client2client/pushkeys.c2c.dart b/lib/src/services/api/client2client/pushkeys.c2c.dart
index 9f2a7072..8d6bfcfb 100644
--- a/lib/src/services/api/client2client/pushkeys.c2c.dart
+++ b/lib/src/services/api/client2client/pushkeys.c2c.dart
@@ -10,10 +10,11 @@ DateTime lastPushKeyRequest = clock.now().subtract(const Duration(hours: 1));
 Future<void> handlePushKey(
   int contactId,
   EncryptedContent_PushKeys pushKeys,
+  String receiptId,
 ) async {
   switch (pushKeys.type) {
     case EncryptedContent_PushKeys_Type.REQUEST:
-      Log.info('Got a pushkey request from $contactId');
+      Log.info('[$receiptId] Got a pushkey request from $contactId');
       if (lastPushKeyRequest.isBefore(
         clock.now().subtract(const Duration(seconds: 60)),
       )) {
@@ -22,7 +23,7 @@ Future<void> handlePushKey(
       }
 
     case EncryptedContent_PushKeys_Type.UPDATE:
-      Log.info('Got a pushkey update from $contactId');
+      Log.info('[$receiptId] Got a pushkey update from $contactId');
       await handleNewPushKey(contactId, pushKeys.keyId.toInt(), pushKeys.key);
   }
 }
diff --git a/lib/src/services/api/client2client/reaction.c2c.dart b/lib/src/services/api/client2client/reaction.c2c.dart
index 77fcdcc3..7988e55b 100644
--- a/lib/src/services/api/client2client/reaction.c2c.dart
+++ b/lib/src/services/api/client2client/reaction.c2c.dart
@@ -8,8 +8,9 @@ Future<void> handleReaction(
   int fromUserId,
   String groupId,
   EncryptedContent_Reaction reaction,
+  String receiptId,
 ) async {
-  Log.info('Got a reaction from $fromUserId (remove=${reaction.remove})');
+  Log.info('[$receiptId] Got a reaction from $fromUserId (remove=${reaction.remove})');
   await twonlyDB.reactionsDao.updateReaction(
     fromUserId,
     reaction.targetMessageId,
diff --git a/lib/src/services/api/client2client/text_message.c2c.dart b/lib/src/services/api/client2client/text_message.c2c.dart
index b46e72f2..7c5cc01c 100644
--- a/lib/src/services/api/client2client/text_message.c2c.dart
+++ b/lib/src/services/api/client2client/text_message.c2c.dart
@@ -11,9 +11,10 @@ Future<void> handleTextMessage(
   int fromUserId,
   String groupId,
   EncryptedContent_TextMessage textMessage,
+  String receiptId,
 ) async {
   Log.info(
-    'Got a text message: ${textMessage.senderMessageId} from $groupId',
+    '[$receiptId] Got a text message: ${textMessage.senderMessageId} from $groupId',
   );
 
   // Prevent message overwrite: reject if a message with this ID already
@@ -23,7 +24,7 @@ Future<void> handleTextMessage(
       .getSingleOrNull();
   if (existing != null && existing.senderId != fromUserId) {
     Log.warn(
-      '$fromUserId tried to overwrite message from ${existing.senderId}. Dropping.',
+      '[$receiptId] $fromUserId tried to overwrite message from ${existing.senderId}. Dropping.',
     );
     return;
   }
@@ -47,6 +48,6 @@ Future<void> handleTextMessage(
     fromTimestamp(textMessage.timestamp),
   );
   if (message != null) {
-    Log.info('Inserted a new text message with ID: ${message.messageId}');
+    Log.info('[$receiptId] Inserted a new text message with ID: ${message.messageId}');
   }
 }
diff --git a/lib/src/services/api/client2client/user_discovery.c2c.dart b/lib/src/services/api/client2client/user_discovery.c2c.dart
index b206109d..e249ff27 100644
--- a/lib/src/services/api/client2client/user_discovery.c2c.dart
+++ b/lib/src/services/api/client2client/user_discovery.c2c.dart
@@ -15,6 +15,7 @@ void resetUserDiscoveryRequestUpdates() {
 Future<void> checkForUserDiscoveryChanges(
   int fromUserId,
   List<int> receivedVersion,
+  String receiptId,
 ) async {
   final currentVersion = await UserDiscoveryService.shouldRequestNewMessages(
     fromUserId,
@@ -26,7 +27,7 @@ Future<void> checkForUserDiscoveryChanges(
       // Only request a new version once per app session
       return;
     }
-    Log.info('Having old version from contact. Requesting new version.');
+    Log.info('[$receiptId] Having old version from contact. Requesting new version.');
     _requestedUpdates.add(fromUserId);
     await sendCipherText(
       fromUserId,
@@ -42,18 +43,19 @@ Future<void> checkForUserDiscoveryChanges(
 Future<void> handleUserDiscoveryRequest(
   int fromUserId,
   EncryptedContent_UserDiscoveryRequest request,
+  String receiptId,
 ) async {
-  Log.info('Got a user discovery request');
+  Log.info('[$receiptId] Got a user discovery request');
 
   if (!userService.currentUser.isUserDiscoveryEnabled) {
-    Log.warn('Got a user discovery request while it is disabled');
+    Log.warn('[$receiptId] Got a user discovery request while it is disabled');
     return;
   }
   final contact = await twonlyDB.contactsDao.getContactById(fromUserId);
 
   if (!UserDiscoveryService.isContactAllowed(contact)) {
     Log.warn(
-      'Got a request to update user discovery, but mediaSendCounter (${contact?.mediaSendCounter}) < ${userService.currentUser.requiredSendImages} or user is excluded ${contact?.userDiscoveryExcluded}',
+      '[$receiptId] Got a request to update user discovery, but mediaSendCounter (${contact?.mediaSendCounter}) < ${userService.currentUser.requiredSendImages} or user is excluded ${contact?.userDiscoveryExcluded}',
     );
     return;
   }
@@ -63,7 +65,7 @@ Future<void> handleUserDiscoveryRequest(
     request.currentVersion,
   );
   if (newMessages != null && newMessages.isNotEmpty) {
-    Log.info('Sending ${newMessages.length} user discovery messages');
+    Log.info('[$receiptId] Sending ${newMessages.length} user discovery messages');
     await sendCipherText(
       fromUserId,
       EncryptedContent(
@@ -73,19 +75,20 @@ Future<void> handleUserDiscoveryRequest(
       ),
     );
   } else {
-    Log.info('Got update request, but there are no new updates for the user');
+    Log.info('[$receiptId] Got update request, but there are no new updates for the user');
   }
 }
 
 Future<void> handleUserDiscoveryUpdate(
   int fromUserId,
   EncryptedContent_UserDiscoveryUpdate update,
+  String receiptId,
 ) async {
   if (!userService.currentUser.isUserDiscoveryEnabled) {
-    Log.warn('Got a user discovery update while it is disabled');
+    Log.warn('[$receiptId] Got a user discovery update while it is disabled');
     return;
   }
-  Log.info('Got ${update.messages.length} user discovery messages');
+  Log.info('[$receiptId] Got ${update.messages.length} user discovery messages');
   await UserDiscoveryService.handleNewMessages(
     fromUserId,
     update.messages.map(Uint8List.fromList).toList(),
diff --git a/lib/src/services/api/mediafiles/upload.api.dart b/lib/src/services/api/mediafiles/upload.api.dart
index 97c8a1fc..da176777 100644
--- a/lib/src/services/api/mediafiles/upload.api.dart
+++ b/lib/src/services/api/mediafiles/upload.api.dart
@@ -35,7 +35,6 @@ Future<void> _protectMediaUpload(
 ) async {
   final mutex = _uploadMutexes.putIfAbsent(mediaId, Mutex.new);
   await mutex.protect(action);
-  _uploadMutexes.remove(mediaId);
 }
 
 Future<void> reuploadMediaFiles() async {
diff --git a/lib/src/services/api/messages.api.dart b/lib/src/services/api/messages.api.dart
index a1baadda..c9ed67e1 100644
--- a/lib/src/services/api/messages.api.dart
+++ b/lib/src/services/api/messages.api.dart
@@ -61,6 +61,8 @@ Future<void> retransmitAllMessages() async {
   });
 }
 
+final Map<String, Mutex> _tryToSendLocks = {};
+
 // When the ackByServerAt is set this value is written in the receipted
 Future<(Uint8List, Uint8List?)?> tryToSendCompleteMessage({
   String? receiptId,
@@ -68,15 +70,41 @@ Future<(Uint8List, Uint8List?)?> tryToSendCompleteMessage({
   bool onlyReturnEncryptedData = false,
   bool blocking = true,
 }) async {
+  final rId = receiptId ?? receipt?.receiptId;
+  if (rId == null) {
+    Log.error(
+      'Cannot try to send complete message as both receiptId and receipt are null.',
+    );
+    return null;
+  }
+
+  final mutex = _tryToSendLocks.putIfAbsent(rId, Mutex.new);
+  return mutex.protect(() async {
+    return _tryToSendCompleteMessageInternal(
+      receiptId: receiptId,
+      receipt: receipt,
+      onlyReturnEncryptedData: onlyReturnEncryptedData,
+      blocking: blocking,
+    );
+  });
+}
+
+Future<(Uint8List, Uint8List?)?> _tryToSendCompleteMessageInternal({
+  String? receiptId,
+  Receipt? receipt,
+  bool onlyReturnEncryptedData = false,
+  bool blocking = true,
+}) async {
+  // this should have a lock for every receiptID, split the function into a _internal withou the lock and a normal with the lock
   if (apiService.appIsOutdated) return null;
+  if (receiptId == null && receipt == null) return null;
 
   try {
-    if (receiptId == null && receipt == null) return null;
     if (receipt == null) {
       // ignore: parameter_assignments
       receipt = await twonlyDB.receiptsDao.getReceiptById(receiptId!);
       if (receipt == null) {
-        Log.warn('Receipt not found.');
+        Log.warn('[$receiptId] Receipt not found.');
         return null;
       }
     }
@@ -120,7 +148,7 @@ Future<(Uint8List, Uint8List?)?> tryToSendCompleteMessage({
       message.encryptedContent,
     );
 
-    Log.info('Uploading ${receipt.receiptId}.');
+    Log.info('Uploading message with receiptID ${receipt.receiptId}.');
 
     Uint8List? pushData;
     if (receipt.retryCount == 0) {
@@ -176,7 +204,7 @@ Future<(Uint8List, Uint8List?)?> tryToSendCompleteMessage({
     );
 
     if (resp.isError) {
-      Log.warn('Could not transmit message got ${resp.error}.');
+      Log.warn('Could not transmit ${receipt.receiptId} got ${resp.error}.');
       if (resp.error == ErrorCode.UserIdNotFound) {
         await twonlyDB.receiptsDao.deleteReceipt(receipt.receiptId);
         await twonlyDB.contactsDao.updateContact(
@@ -210,7 +238,7 @@ Future<(Uint8List, Uint8List?)?> tryToSendCompleteMessage({
       }
     }
   } catch (e) {
-    Log.error('Unknown Error when sending message: $e');
+    Log.error('[$receiptId] unknown error when sending message: $e');
     if (receipt != null) {
       await twonlyDB.receiptsDao.deleteReceipt(receipt.receiptId);
     }
diff --git a/lib/src/services/api/server_messages.api.dart b/lib/src/services/api/server_messages.api.dart
index 8ff3aca6..a66bc9c9 100644
--- a/lib/src/services/api/server_messages.api.dart
+++ b/lib/src/services/api/server_messages.api.dart
@@ -73,7 +73,7 @@ Future<void> handleServerMessage(server.ServerToClient msg) async {
 
   await apiService.sendResponse(ClientToServer()..v0 = v0);
   AppState.gotMessageFromServer = true;
-  Log.info('Message from server proccessed.');
+  Log.info('All messages from the server proccessed.');
 }
 
 DateTime lastPushKeyRequest = clock.now().subtract(const Duration(hours: 1));
@@ -89,7 +89,6 @@ Future<void> handleClient2ClientMessage(NewMessage newMessage) async {
   await mutex.protect(() async {
     await _handleClient2ClientMessage(newMessage, message);
   });
-  _messageLocks.remove(receiptId);
 }
 
 Future<void> _handleClient2ClientMessage(
@@ -103,11 +102,11 @@ Future<void> _handleClient2ClientMessage(
     return;
   }
 
-  Log.info('Started processing message with receiptId $receiptId');
+  Log.info('[$receiptId] Started processing message');
 
   switch (message.type) {
     case Message_Type.SENDER_DELIVERY_RECEIPT:
-      Log.info('Got delivery receipt for $receiptId!');
+      Log.info('[$receiptId] Got delivery receipt!');
       await twonlyDB.receiptsDao.confirmReceipt(receiptId, fromUserId);
 
     case Message_Type.PLAINTEXT_CONTENT:
@@ -120,13 +119,13 @@ Future<void> _handleClient2ClientMessage(
             await handleSessionResync(fromUserId);
           }
           Log.info(
-            'Got decryption error: ${message.plaintextContent.decryptionErrorMessage.type} for $receiptId',
+            '[$receiptId] Got decryption error: ${message.plaintextContent.decryptionErrorMessage.type}',
           );
           retry = true;
         }
         if (message.plaintextContent.hasRetryControlError()) {
           Log.info(
-            'Got access control error for $receiptId. Resending message.',
+            '[$receiptId] Got access control error. Resending message.',
           );
           retry = true;
         }
@@ -141,6 +140,9 @@ Future<void> _handleClient2ClientMessage(
             ackByServerAt: const Value(null),
           ),
         );
+        Log.info(
+          '[$receiptId] Sending error message to the original sender with receiptId $newReceiptId.',
+        );
         await tryToSendCompleteMessage(receiptId: newReceiptId);
       }
 
@@ -197,7 +199,6 @@ Future<void> _handleClient2ClientMessage(
             receiptIdDB = const Value.absent();
           } else {
             // Message was successful processed
-            //
           }
         }
 
@@ -213,7 +214,7 @@ Future<void> _handleClient2ClientMessage(
             ),
           );
         } catch (e) {
-          Log.warn(e);
+          Log.warn('[$receiptId] Error inserting receipt: $e');
         }
         await tryToSendCompleteMessage(receiptId: receiptId);
       }
@@ -223,9 +224,9 @@ Future<void> _handleClient2ClientMessage(
 
   try {
     await twonlyDB.receiptsDao.gotReceipt(receiptId);
-    Log.info('Got a message with receiptId $receiptId');
+    Log.info('[$receiptId] Finished processing');
   } catch (e) {
-    Log.error('Error marking message as received $receiptId: $e');
+    Log.error('[$receiptId] Error marking message as received: $e');
   }
 }
 
@@ -235,26 +236,26 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessageRaw(
   Message_Type messageType,
   String receiptId,
 ) async {
-  final (encryptedContent, decryptionErrorType) = await signalDecryptMessage(
+  Log.info('[$receiptId] calling signalDecryptMessage');
+  var (encryptedContent, decryptionErrorType) = await signalDecryptMessage(
     fromUserId,
     encryptedContentRaw,
     messageType.value,
   );
 
   if (encryptedContent == null) {
-    if (decryptionErrorType == null) {
-      // Duplicate message
-      return (null, null);
-    }
     return (
       null,
-      PlaintextContent()
-        ..decryptionErrorMessage = (PlaintextContent_DecryptionErrorMessage()
-          ..type = decryptionErrorType),
+      PlaintextContent(
+        decryptionErrorMessage: PlaintextContent_DecryptionErrorMessage(
+          type: decryptionErrorType ??=
+              PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
+        ),
+      ),
     );
   }
 
-  Log.info('Calling handleEncryptedMessage for $receiptId');
+  Log.info('[$receiptId] Calling handleEncryptedMessage');
 
   final (a, b) = await handleEncryptedMessage(
     fromUserId,
@@ -263,7 +264,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessageRaw(
     receiptId,
   );
 
-  Log.info('Finished handleEncryptedMessage for $receiptId');
+  Log.info('[$receiptId] Finished handleEncryptedMessage');
 
   if (Platform.isAndroid && a == null && b == null) {
     // Message was handled without any error -> Show push notification to the user.
@@ -294,11 +295,16 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await checkForUserDiscoveryChanges(
       fromUserId,
       content.senderUserDiscoveryVersion,
+      receiptId,
     );
   }
 
   if (content.hasContactRequest()) {
-    if (!await handleContactRequest(fromUserId, content.contactRequest)) {
+    if (!await handleContactRequest(
+      fromUserId,
+      content.contactRequest,
+      receiptId,
+    )) {
       return (
         null,
         PlaintextContent()
@@ -312,6 +318,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await handleErrorMessage(
       fromUserId,
       content.errorMessages,
+      receiptId,
     );
     return (null, null);
   }
@@ -321,6 +328,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.contactUpdate,
       senderProfileCounter,
+      receiptId,
     );
     return (null, null);
   }
@@ -329,6 +337,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await handleUserDiscoveryRequest(
       fromUserId,
       content.userDiscoveryRequest,
+      receiptId,
     );
     return (null, null);
   }
@@ -337,12 +346,13 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await handleUserDiscoveryUpdate(
       fromUserId,
       content.userDiscoveryUpdate,
+      receiptId,
     );
     return (null, null);
   }
 
   if (content.hasPushKeys()) {
-    await handlePushKey(fromUserId, content.pushKeys);
+    await handlePushKey(fromUserId, content.pushKeys, receiptId);
     return (null, null);
   }
 
@@ -350,6 +360,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await handleMessageUpdate(
       fromUserId,
       content.messageUpdate,
+      receiptId,
     );
     return (null, null);
   }
@@ -366,12 +377,13 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     await handleMediaUpdate(
       fromUserId,
       content.mediaUpdate,
+      receiptId,
     );
     return (null, null);
   }
 
   if (!content.hasGroupId()) {
-    Log.error('Messages should have a groupId $fromUserId.');
+    Log.error('[$receiptId] Messages should have a groupId $fromUserId.');
     return (null, null);
   }
 
@@ -380,6 +392,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.groupCreate,
+      receiptId,
     );
     return (null, null);
   }
@@ -392,12 +405,12 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
           .getContactByUserId(fromUserId)
           .getSingleOrNull();
       Log.info(
-        'Contact exists?: ${contact != null} Is deleted? ${contact?.deletedByUser} Accepted? (${contact?.accepted})',
+        '[$receiptId] Contact exists?: ${contact != null} Is deleted? ${contact?.deletedByUser} Accepted? (${contact?.accepted})',
       );
       if (contact == null || !contact.accepted || contact.deletedByUser) {
         await handleNewContactRequest(fromUserId);
         Log.error(
-          'User tries to send message to direct chat while the user does not exists !',
+          '[$receiptId] User tries to send message to direct chat while the user does not exist!',
         );
         return (
           EncryptedContent(
@@ -411,7 +424,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
         );
       }
       Log.info(
-        'Creating new DirectChat between two users',
+        '[$receiptId] Creating new DirectChat between two users',
       );
       await twonlyDB.groupsDao.createNewDirectChat(
         fromUserId,
@@ -422,7 +435,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
     } else {
       if (content.hasGroupJoin()) {
         Log.error(
-          'Got group join message, but group does not exists yet, retry later. As probably the GroupCreate was not yet received.',
+          '[$receiptId] Got group join message, but group does not exist yet, retry later. As probably the GroupCreate was not yet received.',
         );
         // In case the group join was received before the GroupCreate the sender should send it later again.
         return (
@@ -432,13 +445,15 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
         );
       }
 
-      Log.error('User $fromUserId tried to access group ${content.groupId}.');
+      Log.error(
+        '[$receiptId] User $fromUserId tried to access group ${content.groupId}.',
+      );
       return (null, null);
     }
   }
 
   if (content.hasFlameSync()) {
-    await handleFlameSync(content.groupId, content.flameSync);
+    await handleFlameSync(content.groupId, content.flameSync, receiptId);
     return (null, null);
   }
 
@@ -447,6 +462,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.groupUpdate,
+      receiptId,
     );
     return (null, null);
   }
@@ -456,6 +472,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.groupJoin,
+      receiptId,
     )) {
       return (
         null,
@@ -471,6 +488,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.groupJoin,
+      receiptId,
     );
     return (null, null);
   }
@@ -480,6 +498,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.additionalDataMessage,
+      receiptId,
     );
     return (null, null);
   }
@@ -489,6 +508,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.textMessage,
+      receiptId,
     );
     return (null, null);
   }
@@ -498,6 +518,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.reaction,
+      receiptId,
     );
     return (null, null);
   }
@@ -507,6 +528,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.media,
+      receiptId,
     );
     return (null, null);
   }
@@ -516,6 +538,7 @@ Future<(EncryptedContent?, PlaintextContent?)> handleEncryptedMessage(
       fromUserId,
       content.groupId,
       content.typingIndicator,
+      receiptId,
     );
   }
 
diff --git a/lib/src/services/signal/encryption.signal.dart b/lib/src/services/signal/encryption.signal.dart
index abbb1449..facf5fc3 100644
--- a/lib/src/services/signal/encryption.signal.dart
+++ b/lib/src/services/signal/encryption.signal.dart
@@ -42,62 +42,72 @@ signalDecryptMessage(
 ) async {
   // Hold the lock only for the cryptographic operation, not for network I/O
   Log.info('Acquiring lockingSignalProtocol for $fromUserId');
-  final (decryptedContent, errorType, needsResync) = await lockingSignalProtocol
-      .protect(() async {
-        Log.info('Lock acquired for $fromUserId');
-        try {
-          final session = SessionCipher.fromStore(
-            (await getSignalStore())!,
-            getSignalAddress(fromUserId),
-          );
+  final (
+    decryptedContent,
+    errorType,
+    needsResync,
+  ) = await lockingSignalProtocol.protect(() async {
+    Log.info('Lock acquired for $fromUserId');
+    try {
+      final session = SessionCipher.fromStore(
+        (await getSignalStore())!,
+        getSignalAddress(fromUserId),
+      );
 
-          Uint8List plaintext;
+      Uint8List plaintext;
 
-          switch (type) {
-            case CiphertextMessage.prekeyType:
-              plaintext = await session.decrypt(
-                PreKeySignalMessage(encryptedContentRaw),
-              );
-            case CiphertextMessage.whisperType:
-              plaintext = await session.decryptFromSignal(
-                SignalMessage.fromSerialized(encryptedContentRaw),
-              );
-            default:
-              Log.error('Unknown Message Decryption Type: $type');
-              return (
-                null,
-                PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
-                false,
-              );
-          }
-
-          return (EncryptedContent.fromBuffer(plaintext), null, false);
-        } on InvalidKeyIdException catch (e) {
-          Log.warn(e);
-          return (
-            null,
-            PlaintextContent_DecryptionErrorMessage_Type.PREKEY_UNKNOWN,
-            false,
+      switch (type) {
+        case CiphertextMessage.prekeyType:
+          plaintext = await session.decrypt(
+            PreKeySignalMessage(encryptedContentRaw),
           );
-        } on DuplicateMessageException catch (e) {
-          Log.info(e.toString());
-          return (null, null, false);
-        } on InvalidMessageException catch (e) {
-          Log.warn(e);
-          return (
-            null,
-            PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
-            true,
+        case CiphertextMessage.whisperType:
+          plaintext = await session.decryptFromSignal(
+            SignalMessage.fromSerialized(encryptedContentRaw),
           );
-        } catch (e) {
-          Log.error(e);
+        default:
+          Log.error('Unknown Message Decryption Type: $type');
           return (
             null,
             PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
             false,
           );
-        }
-      });
+      }
+
+      return (EncryptedContent.fromBuffer(plaintext), null, false);
+    } on InvalidKeyIdException catch (e) {
+      Log.warn(e);
+      return (
+        null,
+        PlaintextContent_DecryptionErrorMessage_Type.PREKEY_UNKNOWN,
+        false,
+      );
+    } on DuplicateMessageException catch (e) {
+      // This is normal behavior: This can happen in case a message was decrypted, but before further processing
+      // the user killed the app. This results in a new transmission from the server, but as the message was already
+      // decrypted, this error happens. In this case, request the message again.
+      Log.info(e);
+      return (
+        null,
+        PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
+        false,
+      );
+    } on InvalidMessageException catch (e) {
+      Log.warn(e);
+      return (
+        null,
+        PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
+        true,
+      );
+    } catch (e) {
+      Log.error(e);
+      return (
+        null,
+        PlaintextContent_DecryptionErrorMessage_Type.UNKNOWN,
+        false,
+      );
+    }
+  });
 
   Log.info('Released lockingSignalProtocol for $fromUserId');
 
diff --git a/lib/src/utils/log.dart b/lib/src/utils/log.dart
index ae44ca31..d151d3b3 100644
--- a/lib/src/utils/log.dart
+++ b/lib/src/utils/log.dart
@@ -136,7 +136,7 @@ Future<void> cleanLogFile() async {
     }
     final lines = await logFile.readAsLines();
 
-    final twoWeekAgo = clock.now().subtract(const Duration(days: 14));
+    final twoWeekAgo = clock.now().subtract(const Duration(days: 3));
     var keepStartIndex = -1;
 
     for (var i = 0; i < lines.length; i += 100) {
diff --git a/pubspec.lock b/pubspec.lock
index 8b6957f8..fa2fde95 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -2185,7 +2185,7 @@ packages:
     source: hosted
     version: "0.9.1+2"
   workmanager_platform_interface:
-    dependency: transitive
+    dependency: "direct dev"
     description:
       name: workmanager_platform_interface
       sha256: f40422f10b970c67abb84230b44da22b075147637532ac501729256fcea10a47
diff --git a/pubspec.yaml b/pubspec.yaml
index dcf2d3af..0412827e 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -3,7 +3,7 @@ description: "twonly, a privacy-friendly way to connect with friends through sec
 
 publish_to: 'none'
 
-version: 0.2.15+124
+version: 0.2.16+125
 
 environment:
   sdk: ^3.11.0