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 1dffaadc6d69..97c4ca363c77 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
@@ -862,6 +862,11 @@ protected void needsFillInterest()
                             {
                                 interest = true;
                                 _fillState = FillState.INTERESTED;
+                                if (_flushState == FlushState.IDLE && BufferUtil.hasContent(_encryptedOutput))
+                                {
+                                    _flushState = FlushState.WRITING;
+                                    write = _encryptedOutput;
+                                }
                             }
                             break;
 
@@ -1279,9 +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);
+                        }
                     }
                 }
 
@@ -1489,19 +1511,23 @@ private final class IncompleteWriteCallback implements Callback, Invocable
             public void succeeded()
             {
                 boolean fillable;
+                boolean interested;
                 synchronized (_decryptedEndPoint)
                 {
                     if (LOG.isDebugEnabled())
                         LOG.debug("IncompleteWriteCB succeeded {}", SslConnection.this);
-
                     releaseEncryptedOutputBuffer();
                     _flushState = FlushState.IDLE;
+
+                    interested = _fillState == FillState.INTERESTED;
                     fillable = _fillState == FillState.WAIT_FOR_FLUSH;
                     if (fillable)
                         _fillState = FillState.IDLE;
                 }
 
-                if (fillable)
+                if (interested)
+                    ensureFillInterested();
+                else if (fillable)
                     _decryptedEndPoint.getFillInterest().fillable();
 
                 _decryptedEndPoint.getWriteFlusher().completeWrite();
@@ -1520,7 +1546,8 @@ public void failed(final Throwable x)
                     releaseEncryptedOutputBuffer();
 
                     _flushState = FlushState.IDLE;
-                    failFillInterest = _fillState == FillState.WAIT_FOR_FLUSH;
+                    failFillInterest = _fillState == FillState.WAIT_FOR_FLUSH ||
+                        _fillState == FillState.INTERESTED;
                     if (failFillInterest)
                         _fillState = FillState.IDLE;
                 }
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 17a00339d486..3755231dfd33 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));
             }
         }
     }