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 465a3ac8eb93..26b969f545b7 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
@@ -1284,9 +1284,26 @@ public void doShutdownOutput()
                     {
                         // If we still can't flush, but we are not closing the endpoint,
                         // let's just flush the encrypted output in the background.
-                        ByteBuffer write = _encryptedOutput;
-                        if (BufferUtil.hasContent(write))
-                            endPoint.write(Callback.from(Callback.NOOP::succeeded, t -> endPoint.close()), write);
+                        ByteBuffer write = null;
+                        synchronized (_decryptedEndPoint)
+                        {
+                            if (BufferUtil.hasContent(_encryptedOutput))
+                            {
+                                write = _encryptedOutput;
+                                _flushState = FlushState.WRITING;
+                            }
+                        }
+                        if (write != null)
+                        {
+                            endPoint.write(Callback.from(() ->
+                            {
+                                synchronized (_decryptedEndPoint)
+                                {
+                                    _flushState = FlushState.IDLE;
+                                    releaseEncryptedOutputBuffer();
+                                }
+                            }, t -> endPoint.close()), write);
+                        }
                     }
                 }
 
diff --git a/jetty-io/src/test/java/org/eclipse/jetty/io/SslConnectionTest.java b/jetty-io/src/test/java/org/eclipse/jetty/io/SslConnectionTest.java
index 994b2a39f413..6c37691bdb28 100644
--- a/jetty-io/src/test/java/org/eclipse/jetty/io/SslConnectionTest.java
+++ b/jetty-io/src/test/java/org/eclipse/jetty/io/SslConnectionTest.java
@@ -485,9 +485,6 @@ public void testBlockedClose() throws Exception
                 server.configureBlocking(false);
                 _manager.accept(server);
 
-                //__startBlocking.set(5);
-                //__blockFor.set(3);
-
                 client.getOutputStream().write("Short".getBytes(StandardCharsets.UTF_8));
                 byte[] buffer = new byte[1024];
                 int len = client.getInputStream().read(buffer);
@@ -515,7 +512,7 @@ public void testBlockedClose() throws Exception
                 assertTrue(__onIncompleteFlush.get());
                 ((TestEP)_lastEndp).getWriteFlusher().completeWrite();
                 len = client.getInputStream().read(buffer);
-                assertThat(len, is(len));
+                assertThat(len, is(-1));
             }
         }
     }