diff --git a/transport/src/main/java/io/netty/channel/ChannelOutboundBuffer.java b/transport/src/main/java/io/netty/channel/ChannelOutboundBuffer.java
index 5e26506522..9df4eb1558 100644
--- a/transport/src/main/java/io/netty/channel/ChannelOutboundBuffer.java
+++ b/transport/src/main/java/io/netty/channel/ChannelOutboundBuffer.java
@@ -212,18 +212,25 @@ final class ChannelOutboundBuffer {
     }
 
     void clearUnflushed(Throwable cause) {
+        if (inFail) {
+            return;
+        }
+
         MessageList unflushed = unflushedMessageList;
         if (unflushed == null) {
             return;
         }
 
+        inFail = true;
+
         // Release all unflushed messages.
         Object[] messages = unflushed.messages();
         ChannelPromise[] promises = unflushed.promises();
         final int size = unflushed.size();
         try {
             for (int i = 0; i < size; i++) {
-                ReferenceCountUtil.release(messages[i]);
+                safeRelease(messages[i]);
+
                 ChannelPromise p = promises[i];
                 if (!(p instanceof VoidChannelPromise)) {
                     if (!p.tryFailure(cause)) {
@@ -235,6 +242,7 @@ final class ChannelOutboundBuffer {
             unflushed.recycle();
             decrementPendingOutboundBytes(unflushedMessageListSize);
             unflushedMessageListSize = 0;
+            inFail = false;
         }
     }
 
@@ -271,7 +279,8 @@ final class ChannelOutboundBuffer {
                     final int size = current.size();
                     try {
                         for (int i = currentMessageIndex; i < size; i++) {
-                            ReferenceCountUtil.release(messages[i]);
+                            safeRelease(messages[i]);
+
                             ChannelPromise p = promises[i];
                             if (!(p instanceof VoidChannelPromise) && !p.tryFailure(cause)) {
                                 logger.warn("Promise done already: {} - new exception is:", p, cause);
@@ -286,4 +295,12 @@ final class ChannelOutboundBuffer {
             inFail = false;
         }
     }
+
+    private static void safeRelease(Object message) {
+        try {
+            ReferenceCountUtil.release(message);
+        } catch (Throwable t) {
+            logger.warn("Failed to release a message.", t);
+        }
+    }
 }