diff --git a/transport/src/main/java/io/netty/channel/AbstractChannel.java b/transport/src/main/java/io/netty/channel/AbstractChannel.java
index 3449402ab8..7dd9a6e996 100644
--- a/transport/src/main/java/io/netty/channel/AbstractChannel.java
+++ b/transport/src/main/java/io/netty/channel/AbstractChannel.java
@@ -584,10 +584,15 @@ public abstract class AbstractChannel extends DefaultAttributeMap implements Cha
 
         @Override
         public final void close(final ChannelPromise promise) {
+            close(promise, CLOSED_CHANNEL_EXCEPTION, false);
+        }
+
+        private void close(final ChannelPromise promise, final Throwable cause, final boolean notify) {
             if (!promise.setUncancellable()) {
                 return;
             }
 
+            final ChannelOutboundBuffer outboundBuffer = this.outboundBuffer;
             if (outboundBuffer == null) {
                 // Only needed if no VoidChannelPromise.
                 if (!(promise instanceof VoidChannelPromise)) {
@@ -609,8 +614,7 @@ public abstract class AbstractChannel extends DefaultAttributeMap implements Cha
             }
 
             final boolean wasActive = isActive();
-            final ChannelOutboundBuffer buffer = outboundBuffer;
-            outboundBuffer = null; // Disallow adding any messages and flushes to outboundBuffer.
+            this.outboundBuffer = null; // Disallow adding any messages and flushes to outboundBuffer.
             Executor closeExecutor = closeExecutor();
             if (closeExecutor != null) {
                 closeExecutor.execute(new OneTimeTask() {
@@ -625,8 +629,8 @@ public abstract class AbstractChannel extends DefaultAttributeMap implements Cha
                                 @Override
                                 public void run() {
                                     // Fail all the queued messages
-                                    buffer.failFlushed(CLOSED_CHANNEL_EXCEPTION, false);
-                                    buffer.close(CLOSED_CHANNEL_EXCEPTION);
+                                    outboundBuffer.failFlushed(cause, notify);
+                                    outboundBuffer.close(CLOSED_CHANNEL_EXCEPTION);
                                     fireChannelInactiveAndDeregister(wasActive);
                                 }
                             });
@@ -639,8 +643,8 @@ public abstract class AbstractChannel extends DefaultAttributeMap implements Cha
                     doClose0(promise);
                 } finally {
                     // Fail all the queued messages.
-                    buffer.failFlushed(CLOSED_CHANNEL_EXCEPTION, false);
-                    buffer.close(CLOSED_CHANNEL_EXCEPTION);
+                    outboundBuffer.failFlushed(cause, notify);
+                    outboundBuffer.close(CLOSED_CHANNEL_EXCEPTION);
                 }
                 if (inFlush0) {
                     invokeLater(new OneTimeTask() {
@@ -814,11 +818,18 @@ public abstract class AbstractChannel extends DefaultAttributeMap implements Cha
             try {
                 doWrite(outboundBuffer);
             } catch (Throwable t) {
-                boolean close = t instanceof IOException && config().isAutoClose();
-                // We do not want to trigger channelWritabilityChanged event if the channel is going to be closed.
-                outboundBuffer.failFlushed(t, !close);
-                if (close) {
-                    close(voidPromise());
+                if (t instanceof IOException && config().isAutoClose()) {
+                    /**
+                     * Just call {@link #close(ChannelPromise, Throwable, boolean)} here which will take care of
+                     * failing all flushed messages and also ensure the actual close of the underlying transport
+                     * will happen before the promises are notified.
+                     *
+                     * This is needed as otherwise {@link #isActive()} , {@link #isOpen()} and {@link #isWritable()}
+                     * may still return {@code true} even if the channel should be closed as result of the exception.
+                     */
+                    close(voidPromise(), t, false);
+                } else {
+                    outboundBuffer.failFlushed(t, true);
                 }
             } finally {
                 inFlush0 = false;