diff --git a/transport/src/main/java/io/netty/channel/nio/AbstractNioByteChannel.java b/transport/src/main/java/io/netty/channel/nio/AbstractNioByteChannel.java
index 3a42048027..481071cfc0 100644
--- a/transport/src/main/java/io/netty/channel/nio/AbstractNioByteChannel.java
+++ b/transport/src/main/java/io/netty/channel/nio/AbstractNioByteChannel.java
@@ -58,6 +58,12 @@ public abstract class AbstractNioByteChannel extends AbstractNioChannel {
 
         private void removeReadOp() {
             SelectionKey key = selectionKey();
+            // Check first if the key is still valid as it may be canceled as part of the deregistration
+            // from the EventLoop
+            // See https://github.com/netty/netty/issues/2104
+            if (!key.isValid()) {
+                return;
+            }
             int interestOps = key.interestOps();
             if ((interestOps & readInterestOp) != 0) {
                 // only remove readInterestOp if needed
@@ -279,6 +285,12 @@ public abstract class AbstractNioByteChannel extends AbstractNioChannel {
 
     protected final void setOpWrite() {
         final SelectionKey key = selectionKey();
+        // Check first if the key is still valid as it may be canceled as part of the deregistration
+        // from the EventLoop
+        // See https://github.com/netty/netty/issues/2104
+        if (!key.isValid()) {
+            return;
+        }
         final int interestOps = key.interestOps();
         if ((interestOps & SelectionKey.OP_WRITE) == 0) {
             key.interestOps(interestOps | SelectionKey.OP_WRITE);
@@ -287,6 +299,12 @@ public abstract class AbstractNioByteChannel extends AbstractNioChannel {
 
     protected final void clearOpWrite() {
         final SelectionKey key = selectionKey();
+        // Check first if the key is still valid as it may be canceled as part of the deregistration
+        // from the EventLoop
+        // See https://github.com/netty/netty/issues/2104
+        if (!key.isValid()) {
+            return;
+        }
         final int interestOps = key.interestOps();
         if ((interestOps & SelectionKey.OP_WRITE) != 0) {
             key.interestOps(interestOps & ~SelectionKey.OP_WRITE);