diff --git a/analysis_options.yaml b/analysis_options.yaml
index e5eaf7ca..03a4220e 100644
--- a/analysis_options.yaml
+++ b/analysis_options.yaml
@@ -154,18 +154,6 @@ dart_code_metrics:
     # Dart Specific
     - binary-expression-operand-order
     - double-literal-format
-    - prefer-match-file-name:
-        exclude:
-          - packages/*/test/**
-          - packages/*/example/**
-          - packages/**/util/**
-          - packages/**/utils.dart
-          - packages/stream_chat/lib/src/client/client.dart
-          - packages/stream_chat/lib/src/core/api/responses.dart
-          - packages/stream_chat/lib/src/core/api/requests.dart
-          - packages/stream_chat/lib/src/core/platform_detector/**
-          - packages/stream_chat_persistence/lib/src/db/shared/**
-          - packages/stream_chat_localizations/lib/src/stream_chat_localizations.dart
     - no-boolean-literal-compare
     - no-equal-then-else
     - no-empty-block:
diff --git a/packages/stream_chat/CHANGELOG.md b/packages/stream_chat/CHANGELOG.md
index d27ac852..3f20271f 100644
--- a/packages/stream_chat/CHANGELOG.md
+++ b/packages/stream_chat/CHANGELOG.md
@@ -3,7 +3,8 @@
 🐞 Fixed
 
 - [[#799]](https://github.com/GetStream/stream-chat-flutter/issues/799) Fixed `totalUnreadCount` is not updating when
-  app is resumed from background mode
+  app is resumed from background mode.
+- Fix retry mechanism failing in some cases.
 
 ## 3.3.0
 
diff --git a/packages/stream_chat/lib/src/client/channel.dart b/packages/stream_chat/lib/src/client/channel.dart
index 657b8617..51034d3a 100644
--- a/packages/stream_chat/lib/src/client/channel.dart
+++ b/packages/stream_chat/lib/src/client/channel.dart
@@ -1698,7 +1698,7 @@ class ChannelClientState {
       }
 
       _channelState = _channelState.copyWith(
-        messages: newMessages,
+        messages: newMessages..sort(_sortByCreatedAt),
         channel: _channelState.channel?.copyWith(
           lastMessageAt: message.createdAt,
         ),
diff --git a/packages/stream_chat/lib/src/client/retry_queue.dart b/packages/stream_chat/lib/src/client/retry_queue.dart
index c441b5fb..e1b6df70 100644
--- a/packages/stream_chat/lib/src/client/retry_queue.dart
+++ b/packages/stream_chat/lib/src/client/retry_queue.dart
@@ -71,14 +71,15 @@ class RetryQueue {
   /// Add a list of messages
   void add(List<Message> messages) {
     if (messages.isEmpty) return;
-    if (_messageQueue.containsAllMessage(messages)) return;
+    if (!_messageQueue.containsAllMessage(messages)) {
+      logger?.info('Adding ${messages.length} messages');
+      final messageList = _messageQueue.toList();
+      // we should not add message if already available in the queue
+      _messageQueue.addAll(messages.where(
+        (it) => !messageList.any((m) => m.id == it.id),
+      ));
+    }
 
-    logger?.info('Adding ${messages.length} messages');
-    final messageList = _messageQueue.toList();
-    // we should not add message if already available in the queue
-    _messageQueue.addAll(messages.where(
-      (it) => !messageList.any((m) => m.id == it.id),
-    ));
     _startRetrying();
   }
 
@@ -90,17 +91,21 @@ class RetryQueue {
     while (_messageQueue.isNotEmpty) {
       logger?.info('${_messageQueue.length} messages remaining in the queue');
       final message = _messageQueue.first;
-      await _runAndRetry(message);
+      final succeeded = await _runAndRetry(message);
+      if (!succeeded) {
+        _messageQueue.toList().forEach(_sendFailedEvent);
+        break;
+      }
     }
     _isRetrying = false;
   }
 
-  Future<void> _runAndRetry(Message message) async {
+  Future<bool> _runAndRetry(Message message) async {
     var attempt = 1;
 
     final maxAttempt = _retryPolicy.maxRetryAttempts;
     // early return in case maxAttempt is less than 0
-    if (attempt > maxAttempt) return;
+    if (attempt > maxAttempt) return false;
 
     // ignore: literal_only_boolean_expressions
     while (true) {
@@ -109,8 +114,12 @@ class RetryQueue {
         await _retryMessage(message);
         logger?.info('Message (${message.id}) sent successfully');
         _messageQueue.removeMessage(message);
-        break;
-      } on StreamChatError catch (e) {
+        return true;
+      } catch (e) {
+        if (e is! StreamChatNetworkError || !e.isRetriable) {
+          _messageQueue.removeMessage(message);
+          return true;
+        }
         // retry logic
         final maxAttempt = _retryPolicy.maxRetryAttempts;
         if (attempt < maxAttempt) {
@@ -143,16 +152,9 @@ class RetryQueue {
           _sendFailedEvent(message);
           break;
         }
-      } catch (e) {
-        logger?.info(
-          'API call failed due to unknown error (attempt $attempt). '
-          'Giving up for now, will retry when connection recovers. '
-          'Error was $e',
-        );
-        _sendFailedEvent(message);
-        break;
       }
     }
+    return false;
   }
 
   void _sendFailedEvent(Message message) {
diff --git a/packages/stream_chat_flutter/lib/src/message_widget.dart b/packages/stream_chat_flutter/lib/src/message_widget.dart
index 6182df54..4010b11b 100644
--- a/packages/stream_chat_flutter/lib/src/message_widget.dart
+++ b/packages/stream_chat_flutter/lib/src/message_widget.dart
@@ -832,8 +832,8 @@ class _MessageWidgetState extends State<MessageWidget>
                         ),
                       if (isFailedState)
                         Positioned(
-                          left: widget.reverse ? 0 : null,
-                          right: widget.reverse ? null : 0,
+                          right: widget.reverse ? 0 : null,
+                          left: widget.reverse ? null : 0,
                           bottom: showBottomRow ? 18 : -2,
                           child: StreamSvgIcon.error(size: 20),
                         ),