diff --git a/jetty-client/src/test/java/org/eclipse/jetty/client/HttpClientTLSTest.java b/jetty-client/src/test/java/org/eclipse/jetty/client/HttpClientTLSTest.java
index 88fa504e269..a930c5d9f21 100644
--- a/jetty-client/src/test/java/org/eclipse/jetty/client/HttpClientTLSTest.java
+++ b/jetty-client/src/test/java/org/eclipse/jetty/client/HttpClientTLSTest.java
@@ -35,7 +35,9 @@ import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicLong;
 import java.util.concurrent.atomic.AtomicReference;
 import javax.net.ssl.SSLEngine;
+import javax.net.ssl.SSLEngineResult;
 import javax.net.ssl.SSLException;
+import javax.net.ssl.SSLHandshakeException;
 import javax.net.ssl.SSLPeerUnverifiedException;
 import javax.net.ssl.SSLSocket;
 
@@ -63,6 +65,7 @@ import org.eclipse.jetty.util.StringUtil;
 import org.eclipse.jetty.util.ssl.SslContextFactory;
 import org.eclipse.jetty.util.thread.ExecutorThreadPool;
 import org.eclipse.jetty.util.thread.QueuedThreadPool;
+import org.hamcrest.Matchers;
 import org.junit.jupiter.api.AfterEach;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.condition.EnabledOnJre;
@@ -772,4 +775,52 @@ public class HttpClientTLSTest
         assertEquals(0, serverBytes.get());
         assertEquals(0, clientBytes.get());
     }
+
+    @Test
+    public void testSSLEngineClosedDuringHandshake() throws Exception
+    {
+        SslContextFactory.Server serverTLSFactory = createServerSslContextFactory();
+        startServer(serverTLSFactory, new EmptyServerHandler());
+
+        SslContextFactory.Client clientTLSFactory = createClientSslContextFactory();
+        ClientConnector clientConnector = new ClientConnector();
+        clientConnector.setSelectors(1);
+        clientConnector.setSslContextFactory(clientTLSFactory);
+        QueuedThreadPool clientThreads = new QueuedThreadPool();
+        clientThreads.setName("client");
+        clientConnector.setExecutor(clientThreads);
+        client = new HttpClient(new HttpClientTransportOverHTTP(clientConnector))
+        {
+            @Override
+            protected ClientConnectionFactory newSslClientConnectionFactory(SslContextFactory.Client sslContextFactory, ClientConnectionFactory connectionFactory)
+            {
+                if (sslContextFactory == null)
+                    sslContextFactory = getSslContextFactory();
+                return new SslClientConnectionFactory(sslContextFactory, getByteBufferPool(), getExecutor(), connectionFactory)
+                {
+                    @Override
+                    protected SslConnection newSslConnection(ByteBufferPool byteBufferPool, Executor executor, EndPoint endPoint, SSLEngine engine)
+                    {
+                        return new SslConnection(byteBufferPool, executor, endPoint, engine, isDirectBuffersForEncryption(), isDirectBuffersForDecryption())
+                        {
+                            @Override
+                            protected SSLEngineResult wrap(SSLEngine sslEngine, ByteBuffer[] input, ByteBuffer output) throws SSLException
+                            {
+                                sslEngine.closeOutbound();
+                                return super.wrap(sslEngine, input, output);
+                            }
+                        };
+                    }
+                };
+            }
+        };
+        client.setExecutor(clientThreads);
+        client.start();
+
+        ExecutionException failure = assertThrows(ExecutionException.class, () -> client.newRequest("localhost", connector.getLocalPort())
+            .scheme(HttpScheme.HTTPS.asString())
+            .send());
+        Throwable cause = failure.getCause();
+        assertThat(cause, Matchers.instanceOf(SSLHandshakeException.class));
+    }
 }
diff --git a/jetty-io/src/main/java/org/eclipse/jetty/io/ssl/SslConnection.java b/jetty-io/src/main/java/org/eclipse/jetty/io/ssl/SslConnection.java
index 3f8b445fe07..745b286b8f1 100644
--- a/jetty-io/src/main/java/org/eclipse/jetty/io/ssl/SslConnection.java
+++ b/jetty-io/src/main/java/org/eclipse/jetty/io/ssl/SslConnection.java
@@ -358,6 +358,16 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
         _decryptedEndPoint.onFillableFail(cause == null ? new IOException() : cause);
     }
 
+    protected SSLEngineResult wrap(SSLEngine sslEngine, ByteBuffer[] input, ByteBuffer output) throws SSLException
+    {
+        return sslEngine.wrap(input, output);
+    }
+
+    protected SSLEngineResult unwrap(SSLEngine sslEngine, ByteBuffer input, ByteBuffer output) throws SSLException
+    {
+        return sslEngine.unwrap(input, output);
+    }
+
     @Override
     public String toConnectionString()
     {
@@ -621,7 +631,7 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
                             try
                             {
                                 _underflown = false;
-                                unwrapResult = _sslEngine.unwrap(_encryptedInput, appIn);
+                                unwrapResult = unwrap(_sslEngine, _encryptedInput, appIn);
                             }
                             finally
                             {
@@ -696,8 +706,8 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
                     }
                     catch (Throwable x)
                     {
-                        Throwable failure = handleException(x, "fill");
-                        handshakeFailed(failure);
+                        Throwable f = handleException(x, "fill");
+                        Throwable failure = handshakeFailed(f);
                         if (_flushState == FlushState.WAIT_FOR_FILL)
                         {
                             _flushState = FlushState.IDLE;
@@ -834,7 +844,7 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
             }
         }
 
-        private void handshakeFailed(Throwable failure)
+        private Throwable handshakeFailed(Throwable failure)
         {
             if (_handshake.compareAndSet(HandshakeState.HANDSHAKE, HandshakeState.FAILED))
             {
@@ -844,6 +854,7 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
                     failure = new SSLHandshakeException(failure.getMessage()).initCause(failure);
                 notifyHandshakeFailed(_sslEngine, failure);
             }
+            return failure;
         }
 
         private void terminateInput()
@@ -958,7 +969,7 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
                             SSLEngineResult wrapResult;
                             try
                             {
-                                wrapResult = _sslEngine.wrap(appOuts, _encryptedOutput);
+                                wrapResult = wrap(_sslEngine, appOuts, _encryptedOutput);
                             }
                             finally
                             {
@@ -1037,8 +1048,7 @@ public class SslConnection extends AbstractConnection implements Connection.Upgr
                     catch (Throwable x)
                     {
                         Throwable failure = handleException(x, "flush");
-                        handshakeFailed(failure);
-                        throw failure;
+                        throw handshakeFailed(failure);
                     }
                     finally
                     {