diff --git a/jetty-core/jetty-websocket/jetty-websocket-core-common/src/main/java/org/eclipse/jetty/websocket/core/internal/PerMessageDeflateExtension.java b/jetty-core/jetty-websocket/jetty-websocket-core-common/src/main/java/org/eclipse/jetty/websocket/core/internal/PerMessageDeflateExtension.java
index 2f8f54eb6d6..14cb66a15e3 100644
--- a/jetty-core/jetty-websocket/jetty-websocket-core-common/src/main/java/org/eclipse/jetty/websocket/core/internal/PerMessageDeflateExtension.java
+++ b/jetty-core/jetty-websocket/jetty-websocket-core-common/src/main/java/org/eclipse/jetty/websocket/core/internal/PerMessageDeflateExtension.java
@@ -470,14 +470,25 @@ public class PerMessageDeflateExtension extends AbstractExtension implements Dem
             chunk.setPayload(byteBuffer);
             chunk.setFin(frame.isFin() && complete);
 
-            // Capture the current AtomicReference.
+            // If we are complete we return true, then DemandingFlusher.process() will null out the Frame and Callback.
+            // The application may decide to hold onto the buffer and delay completing the callback, so we need to capture
+            // references to these in the payloadCallback and not rely on state of the flusher which may have moved on.
+            // This flusher could be failed while the application already has the payloadCallback, so we need protection against
+            // the flusher failing and the application completing the callback, that's why we use the payload AtomicReference.
+            boolean completeCallback = complete;
             AtomicReference<RetainableByteBuffer> payloadRef = _payloadRef;
-            boolean succeedCallback = complete;
-            Callback payloadCallback = Callback.from(() -> releasePayload(payloadRef), Callback.from(() ->
+            Callback payloadCallback = Callback.from(() ->
             {
-                if (succeedCallback)
+                releasePayload(payloadRef);
+                if (completeCallback)
                     callback.succeeded();
-            }, this::failFlusher));
+            }, t ->
+            {
+                releasePayload(payloadRef);
+                if (completeCallback)
+                    callback.failed(t);
+                failFlusher(t);
+            });
 
             emitFrame(chunk, payloadCallback);
             if (LOG.isDebugEnabled())
diff --git a/jetty-ee9/jetty-ee9-websocket/jetty-ee9-websocket-jetty-tests/src/test/java/org/eclipse/jetty/ee9/websocket/tests/LargeDeflateTest.java b/jetty-ee9/jetty-ee9-websocket/jetty-ee9-websocket-jetty-tests/src/test/java/org/eclipse/jetty/ee9/websocket/tests/LargeDeflateTest.java
index d3d36b71ebf..1bb9a218219 100644
--- a/jetty-ee9/jetty-ee9-websocket/jetty-ee9-websocket-jetty-tests/src/test/java/org/eclipse/jetty/ee9/websocket/tests/LargeDeflateTest.java
+++ b/jetty-ee9/jetty-ee9-websocket/jetty-ee9-websocket-jetty-tests/src/test/java/org/eclipse/jetty/ee9/websocket/tests/LargeDeflateTest.java
@@ -33,6 +33,7 @@ import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
 
 import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.Matchers.containsString;
 import static org.hamcrest.Matchers.is;
 import static org.junit.jupiter.api.Assertions.assertTrue;
 
@@ -92,6 +93,27 @@ public class LargeDeflateTest
         assertThat(message, is(sentMessage));
     }
 
+    @Test
+    void testDeflateLargerThanMaxMessage() throws Exception
+    {
+        ClientUpgradeRequest upgradeRequest = new ClientUpgradeRequest();
+        upgradeRequest.addExtensions("permessage-deflate");
+
+        EventSocket clientSocket = new EventSocket();
+        ByteBuffer message = largePayloads();
+        Session session = _client.connect(clientSocket, URI.create("ws://localhost:" + _connector.getLocalPort() + "/ws"), upgradeRequest).get();
+
+        // Set the maxBinaryMessageSize on the server to be lower than the size of the message.
+        assertTrue(_serverSocket.openLatch.await(5, TimeUnit.SECONDS));
+        _serverSocket.session.setMaxBinaryMessageSize(message.remaining() - 1024);
+
+        session.getRemote().sendBytes(message);
+        assertTrue(clientSocket.closeLatch.await(5, TimeUnit.SECONDS));
+        assertTrue(_serverSocket.closeLatch.await(5, TimeUnit.SECONDS));
+        assertThat(_serverSocket.closeCode, is(StatusCode.MESSAGE_TOO_LARGE));
+        assertThat(_serverSocket.closeReason, containsString("Binary message too large"));
+    }
+
     private static ByteBuffer largePayloads()
     {
         var bytes = new byte[4 * 1024 * 1024];