diff --git a/jetty-client/src/test/java/org/eclipse/jetty/client/HostnameVerificationTest.java b/jetty-client/src/test/java/org/eclipse/jetty/client/HostnameVerificationTest.java
index b909749a4c9..a6c48ee5e05 100644
--- a/jetty-client/src/test/java/org/eclipse/jetty/client/HostnameVerificationTest.java
+++ b/jetty-client/src/test/java/org/eclipse/jetty/client/HostnameVerificationTest.java
@@ -49,13 +49,17 @@ import org.junit.Test;
 public class HostnameVerificationTest
 {
     private SslContextFactory clientSslContextFactory = new SslContextFactory();
-    private Server server = new Server();
+    private Server server;
     private HttpClient client;
     private NetworkConnector connector;
 
     @Before
     public void setUp() throws Exception
     {
+        QueuedThreadPool serverThreads = new QueuedThreadPool();
+        serverThreads.setName("server");
+        server = new Server(serverThreads);
+
         SslContextFactory serverSslContextFactory = new SslContextFactory();
         serverSslContextFactory.setKeyStorePath("src/test/resources/keystore.jks");
         serverSslContextFactory.setKeyStorePassword("storepwd");
@@ -76,10 +80,10 @@ public class HostnameVerificationTest
         clientSslContextFactory.setKeyStorePath("src/test/resources/keystore.jks");
         clientSslContextFactory.setKeyStorePassword("storepwd");
 
-        QueuedThreadPool executor = new QueuedThreadPool();
-        executor.setName(executor.getName() + "-client");
+        QueuedThreadPool clientThreads = new QueuedThreadPool();
+        clientThreads.setName("client");
         client = new HttpClient(clientSslContextFactory);
-        client.setExecutor(executor);
+        client.setExecutor(clientThreads);
         client.start();
     }
 
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 18526f84de7..3071e7f59e9 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
@@ -579,6 +579,7 @@ public class SslConnection extends AbstractConnection
             {
                 synchronized (this)
                 {
+                    Throwable failure = null;
                     try
                     {
                         // Do we already have some decrypted data?
@@ -773,6 +774,7 @@ public class SslConnection extends AbstractConnection
                     catch (SSLHandshakeException x)
                     {
                         notifyHandshakeFailed(_sslEngine, x);
+                        failure = x;
                         throw x;
                     }
                     catch (SSLException x)
@@ -782,6 +784,12 @@ public class SslConnection extends AbstractConnection
                             x = (SSLException)new SSLHandshakeException(x.getMessage()).initCause(x);
                             notifyHandshakeFailed(_sslEngine, x);
                         }
+                        failure = x;
+                        throw x;
+                    }
+                    catch (Throwable x)
+                    {
+                        failure = x;
                         throw x;
                     }
                     finally
@@ -790,7 +798,7 @@ public class SslConnection extends AbstractConnection
                         if (_flushRequiresFillToProgress)
                         {
                             _flushRequiresFillToProgress = false;
-                            getExecutor().execute(_runCompleteWrite);
+                            getExecutor().execute(failure == null ? _runCompleteWrite : new FailWrite(failure));
                         }
 
                         if (_encryptedInput != null && !_encryptedInput.hasRemaining())
@@ -1132,5 +1140,28 @@ public class SslConnection extends AbstractConnection
         {
             return super.toString()+"->"+getEndPoint().toString();
         }
+
+        private class FailWrite extends RunnableTask
+        {
+            private final Throwable failure;
+
+            private FailWrite(Throwable failure)
+            {
+                super("runFailWrite");
+                this.failure = failure;
+            }
+
+            @Override
+            public void run()
+            {
+                getWriteFlusher().onFail(failure);
+            }
+
+            @Override
+            public InvocationType getInvocationType()
+            {
+                return getWriteFlusher().getCallbackInvocationType();
+            }
+        }
     }
 }
diff --git a/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/AsyncIOServletTest.java b/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/AsyncIOServletTest.java
index 393f4197ac4..af1c90507ff 100644
--- a/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/AsyncIOServletTest.java
+++ b/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/AsyncIOServletTest.java
@@ -1137,6 +1137,10 @@ public class AsyncIOServletTest extends AbstractTest
                 break;
             case H2C:
             case H2:
+                // In case of HTTP/2, we not only send the request, but also the preface and
+                // SETTINGS frames. SETTINGS frame need to be replied, so we want to wait to
+                // write the reply before shutting output down, so that the test does not fail.
+                Thread.sleep(1000);
                 Session session = ((HttpConnectionOverHTTP2)connection).getSession();
                 ((HTTP2Session)session).getEndPoint().shutdownOutput();
                 break;