diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTConnectionManager.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTConnectionManager.java
index be42d2fefb..9800be5ee4 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTConnectionManager.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTConnectionManager.java
@@ -26,7 +26,6 @@ import io.netty.buffer.ByteBufAllocator;
 import io.netty.handler.codec.mqtt.MqttConnectReturnCode;
 import org.apache.activemq.artemis.api.core.client.ActiveMQClient;
 import org.apache.activemq.artemis.core.server.ActiveMQServer;
-import org.apache.activemq.artemis.core.server.ServerMessage;
 import org.apache.activemq.artemis.core.server.ServerSession;
 import org.apache.activemq.artemis.core.server.impl.ServerSessionImpl;
 import org.apache.activemq.artemis.utils.ConcurrentHashSet;
@@ -45,6 +44,16 @@ public class MQTTConnectionManager {
 
    private MQTTLogger log = MQTTLogger.LOGGER;
 
+   private boolean isWill = false;
+
+   private ByteBuf willMessage;
+
+   private String willTopic;
+
+   private int willQoSLevel;
+
+   private boolean willRetain;
+
    public MQTTConnectionManager(MQTTSession session) {
       this.session = session;
       MQTTFailureListener failureListener = new MQTTFailureListener(this);
@@ -66,7 +75,7 @@ public class MQTTConnectionManager {
       String clientId = validateClientId(cId, cleanSession);
       if (clientId == null) {
          session.getProtocolHandler().sendConnack(MqttConnectReturnCode.CONNECTION_REFUSED_IDENTIFIER_REJECTED);
-         session.getProtocolHandler().disconnect();
+         session.getProtocolHandler().disconnect(true);
          return;
       }
 
@@ -78,11 +87,13 @@ public class MQTTConnectionManager {
       session.setIsClean(cleanSession);
 
       if (will) {
+         isWill = true;
          byte[] payload = willMessage.getBytes(Charset.forName("UTF-8"));
-         ByteBuf buf = ByteBufAllocator.DEFAULT.buffer(payload.length);
-         buf.writeBytes(payload);
-         ServerMessage w = MQTTUtil.createServerMessageFromByteBuf(session, willTopic, willRetain, willQosLevel, buf);
-         session.getSessionState().setWillMessage(w);
+         this.willMessage = ByteBufAllocator.DEFAULT.buffer(payload.length);
+         this.willMessage.writeBytes(payload);
+         this.willQoSLevel = willQosLevel;
+         this.willRetain = willRetain;
+         this.willTopic = willTopic;
       }
 
       session.getConnection().setConnected(true);
@@ -119,18 +130,17 @@ public class MQTTConnectionManager {
       return (ServerSessionImpl) serverSession;
    }
 
-   synchronized void disconnect() {
-      if (session == null) {
+   synchronized void disconnect(boolean failure) {
+      if (session == null || session.getStopped()) {
          return;
       }
 
       try {
+         if (isWill && failure) {
+            session.getMqttPublishManager().sendInternal(0, willTopic, willQoSLevel, willMessage, willRetain, true);
+         }
          session.stop();
          session.getConnection().destroy();
-
-         if (session.getState().isWill()) {
-            session.getConnectionManager().sendWill();
-         }
       } catch (Exception e) {
          log.error("Error disconnecting client: " + e.getMessage());
       } finally {
@@ -144,11 +154,6 @@ public class MQTTConnectionManager {
       }
    }
 
-   private void sendWill() throws Exception {
-      session.getServer().getPostOffice().route(session.getSessionState().getWillMessage(), true);
-      session.getSessionState().deleteWillMessage();
-   }
-
    private MQTTSessionState getSessionState(String clientId) throws InterruptedException {
       /* [MQTT-3.1.2-6] If CleanSession is set to 1, the Client and Server MUST discard any previous Session and
        * start a new one  This Session lasts as long as the Network Connection. State data associated with this Session
diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTFailureListener.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTFailureListener.java
index 7bd9fadae5..4a98d159aa 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTFailureListener.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTFailureListener.java
@@ -34,11 +34,11 @@ public class MQTTFailureListener implements FailureListener {
 
    @Override
    public void connectionFailed(ActiveMQException exception, boolean failedOver) {
-      connectionManager.disconnect();
+      connectionManager.disconnect(true);
    }
 
    @Override
    public void connectionFailed(ActiveMQException exception, boolean failedOver, String scaleDownTargetNodeID) {
-      connectionManager.disconnect();
+      connectionManager.disconnect(true);
    }
 }
diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTProtocolHandler.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTProtocolHandler.java
index b3587a3a2d..b084f9d067 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTProtocolHandler.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTProtocolHandler.java
@@ -39,9 +39,9 @@ import io.netty.handler.codec.mqtt.MqttSubAckPayload;
 import io.netty.handler.codec.mqtt.MqttSubscribeMessage;
 import io.netty.handler.codec.mqtt.MqttUnsubAckMessage;
 import io.netty.handler.codec.mqtt.MqttUnsubscribeMessage;
+import org.apache.activemq.artemis.api.core.RoutingType;
 import org.apache.activemq.artemis.api.core.SimpleString;
 import org.apache.activemq.artemis.core.server.ActiveMQServer;
-import org.apache.activemq.artemis.api.core.RoutingType;
 import org.apache.activemq.artemis.spi.core.protocol.ConnectionEntry;
 
 /**
@@ -89,7 +89,7 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
    public void channelRead(ChannelHandlerContext ctx, Object msg) {
       try {
          if (stopped) {
-            disconnect();
+            disconnect(true);
             return;
          }
 
@@ -98,7 +98,7 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
          // Disconnect if Netty codec failed to decode the stream.
          if (message.decoderResult().isFailure()) {
             log.debug("Bad Message Disconnecting Client.");
-            disconnect();
+            disconnect(true);
             return;
          }
 
@@ -150,11 +150,11 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
                handleDisconnect(message);
                break;
             default:
-               disconnect();
+               disconnect(true);
          }
       } catch (Exception e) {
          log.debug("Error processing Control Packet, Disconnecting Client", e);
-         disconnect();
+         disconnect(true);
       }
    }
 
@@ -171,8 +171,8 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
       session.getConnectionManager().connect(clientId, connect.payload().userName(), connect.payload().password(), connect.variableHeader().isWillFlag(), connect.payload().willMessage(), connect.payload().willTopic(), connect.variableHeader().isWillRetain(), connect.variableHeader().willQos(), connect.variableHeader().isCleanSession());
    }
 
-   void disconnect() {
-      session.getConnectionManager().disconnect();
+   void disconnect(boolean error) {
+      session.getConnectionManager().disconnect(error);
    }
 
    void sendConnack(MqttConnectReturnCode returnCode) {
@@ -193,7 +193,7 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
    void handleConnack(MqttConnAckMessage message) {
       log.debug("Received invalid CONNACK from client: " + session.getSessionState().getClientId());
       log.debug("Disconnecting client: " + session.getSessionState().getClientId());
-      disconnect();
+      disconnect(true);
    }
 
    void handlePublish(MqttPublishMessage message) throws Exception {
@@ -257,7 +257,7 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
    }
 
    void handleSuback(MqttSubAckMessage message) {
-      disconnect();
+      disconnect(true);
    }
 
    void handleUnsubscribe(MqttUnsubscribeMessage message) throws Exception {
@@ -270,7 +270,7 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
    }
 
    void handleUnsuback(MqttUnsubAckMessage message) {
-      disconnect();
+      disconnect(true);
    }
 
    void handlePingreq(MqttMessage message, ChannelHandlerContext ctx) {
@@ -281,13 +281,11 @@ public class MQTTProtocolHandler extends ChannelInboundHandlerAdapter {
    }
 
    void handlePingresp(MqttMessage message) {
-      disconnect();
+      disconnect(true);
    }
 
    void handleDisconnect(MqttMessage message) {
-      if (session.getSessionState() != null)
-         session.getState().deleteWillMessage();
-      disconnect();
+      disconnect(false);
    }
 
    protected int send(int messageId, String topicName, int qosLevel, ByteBuf payload, int deliveryCount) {
diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTPublishManager.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTPublishManager.java
index 26886c6db9..76f15c0938 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTPublishManager.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTPublishManager.java
@@ -32,6 +32,7 @@ import org.apache.activemq.artemis.core.server.Queue;
 import org.apache.activemq.artemis.core.server.ServerConsumer;
 import org.apache.activemq.artemis.core.server.ServerMessage;
 import org.apache.activemq.artemis.core.server.impl.ServerMessageImpl;
+import org.apache.activemq.artemis.core.transaction.Transaction;
 
 /**
  * Handles MQTT Exactly Once (QoS level 2) Protocol.
@@ -133,6 +134,20 @@ public class MQTTPublishManager {
 
    // INBOUND
    void handleMessage(int messageId, String topic, int qos, ByteBuf payload, boolean retain) throws Exception {
+      sendInternal(messageId, topic, qos, payload, retain, false);
+   }
+
+   /**
+    * Sends a message either on behalf of the client or on behalf of the broker (Will Messages)
+    * @param messageId
+    * @param topic
+    * @param qos
+    * @param payload
+    * @param retain
+    * @param internal if true means on behalf of the broker (skips authorisation) and does not return ack.
+    * @throws Exception
+    */
+   void sendInternal(int messageId, String topic, int qos, ByteBuf payload, boolean retain, boolean internal) throws Exception {
       synchronized (lock) {
          ServerMessage serverMessage = MQTTUtil.createServerMessageFromByteBuf(session, topic, retain, qos, payload);
 
@@ -141,17 +156,23 @@ public class MQTTPublishManager {
          }
 
          if (qos < 2 || !state.getPubRec().contains(messageId)) {
-            if (qos == 2)
+            if (qos == 2 && !internal)
                state.getPubRec().add(messageId);
-            session.getServerSession().send(serverMessage, true);
-         }
 
-         if (retain) {
-            boolean reset = payload instanceof EmptyByteBuf || payload.capacity() == 0;
-            session.getRetainMessageManager().handleRetainedMessage(serverMessage, topic, reset);
+            Transaction tx = session.getServerSession().newTransaction();
+            try {
+               session.getServerSession().send(tx, serverMessage, true, false);
+               if (retain) {
+                  boolean reset = payload instanceof EmptyByteBuf || payload.capacity() == 0;
+                  session.getRetainMessageManager().handleRetainedMessage(serverMessage, topic, reset, tx);
+               }
+               tx.commit();
+            } catch (Throwable t) {
+               tx.rollback();
+               throw t;
+            }
+            createMessageAck(messageId, qos, internal);
          }
-
-         createMessageAck(messageId, qos);
       }
    }
 
@@ -182,14 +203,16 @@ public class MQTTPublishManager {
       }
    }
 
-   private void createMessageAck(final int messageId, final int qos) {
+   private void createMessageAck(final int messageId, final int qos, final boolean internal) {
       session.getServer().getStorageManager().afterCompleteOperations(new IOCallback() {
          @Override
          public void done() {
-            if (qos == 1) {
-               session.getProtocolHandler().sendPubAck(messageId);
-            } else if (qos == 2) {
-               session.getProtocolHandler().sendPubRec(messageId);
+            if (!internal) {
+               if (qos == 1) {
+                  session.getProtocolHandler().sendPubAck(messageId);
+               } else if (qos == 2) {
+                  session.getProtocolHandler().sendPubRec(messageId);
+               }
             }
          }
 
diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTRetainMessageManager.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTRetainMessageManager.java
index 27423d8452..596670bf94 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTRetainMessageManager.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTRetainMessageManager.java
@@ -17,13 +17,15 @@
 
 package org.apache.activemq.artemis.core.protocol.mqtt;
 
-import java.util.Iterator;
-
 import org.apache.activemq.artemis.api.core.SimpleString;
 import org.apache.activemq.artemis.core.server.BindingQueryResult;
 import org.apache.activemq.artemis.core.server.MessageReference;
 import org.apache.activemq.artemis.core.server.Queue;
+import org.apache.activemq.artemis.core.server.RoutingContext;
 import org.apache.activemq.artemis.core.server.ServerMessage;
+import org.apache.activemq.artemis.core.server.impl.RoutingContextImpl;
+import org.apache.activemq.artemis.core.transaction.Transaction;
+import org.apache.activemq.artemis.utils.LinkedListIterator;
 
 public class MQTTRetainMessageManager {
 
@@ -42,7 +44,7 @@ public class MQTTRetainMessageManager {
     * the subscription queue for the consumer.  When a new retained message is received the message will be sent to
     * the retained queue and the previous retain message consumed to remove it from the queue.
     */
-   void handleRetainedMessage(ServerMessage message, String address, boolean reset) throws Exception {
+   void handleRetainedMessage(ServerMessage message, String address, boolean reset, Transaction tx) throws Exception {
       SimpleString retainAddress = new SimpleString(MQTTUtil.convertMQTTAddressFilterToCoreRetain(address, session.getWildcardConfiguration()));
 
       Queue queue = session.getServer().locateQueue(retainAddress);
@@ -50,39 +52,52 @@ public class MQTTRetainMessageManager {
          queue = session.getServerSession().createQueue(retainAddress, retainAddress, null, false, true);
       }
 
-      // Set the address of this message to the retained queue.
-      message.setAddress(retainAddress);
 
-      Iterator<MessageReference> iterator = queue.iterator();
-      synchronized (iterator) {
-         if (iterator.hasNext()) {
-            Long messageId = iterator.next().getMessage().getMessageID();
-            queue.deleteReference(messageId);
-         }
+      try (LinkedListIterator<MessageReference> iterator = queue.iterator()) {
+         synchronized (queue) {
+            if (iterator.hasNext()) {
+               MessageReference ref = iterator.next();
+               iterator.remove();
+               queue.acknowledge(tx, ref);
+            }
 
-         if (!reset) {
-            session.getServerSession().send(message.copy(), true);
-         }
-      }
-   }
-
-   void addRetainedMessagesToQueue(Queue queue, String address) throws Exception {
-      // Queue to add the retained messages to
-
-      // The address filter that matches all retained message queues.
-      String retainAddress = MQTTUtil.convertMQTTAddressFilterToCoreRetain(address, session.getWildcardConfiguration());
-      BindingQueryResult bindingQueryResult = session.getServerSession().executeBindingQuery(new SimpleString(retainAddress));
-
-      // Iterate over all matching retain queues and add the head message to the original queue.
-      for (SimpleString retainedQueueName : bindingQueryResult.getQueueNames()) {
-         Queue retainedQueue = session.getServer().locateQueue(retainedQueueName);
-         synchronized (this) {
-            Iterator<MessageReference> i = retainedQueue.iterator();
-            if (i.hasNext()) {
-               ServerMessage message = i.next().getMessage().copy(session.getServer().getStorageManager().generateID());
-               queue.addTail(message.createReference(queue), true);
+            if (!reset) {
+               sendToQueue(message.copy(session.getServer().getStorageManager().generateID()), queue, tx);
             }
          }
       }
    }
+
+   // SEND to Queue.
+   void addRetainedMessagesToQueue(Queue queue, String address) throws Exception {
+      // The address filter that matches all retained message queues.
+      String retainAddress = MQTTUtil.convertMQTTAddressFilterToCoreRetain(address, session.getWildcardConfiguration());
+      BindingQueryResult bindingQueryResult = session.getServerSession().executeBindingQuery(new SimpleString(retainAddress));
+
+      // Iterate over all matching retain queues and add the queue
+      Transaction tx = session.getServerSession().newTransaction();
+      try {
+         synchronized (queue) {
+            for (SimpleString retainedQueueName : bindingQueryResult.getQueueNames()) {
+               Queue retainedQueue = session.getServer().locateQueue(retainedQueueName);
+               try (LinkedListIterator<MessageReference> i = retainedQueue.iterator()) {
+                  if (i.hasNext()) {
+                     ServerMessage message = i.next().getMessage().copy(session.getServer().getStorageManager().generateID());
+                     sendToQueue(message, queue, tx);
+                  }
+               }
+            }
+         }
+      } catch (Throwable t) {
+         tx.rollback();
+         throw t;
+      }
+      tx.commit();
+   }
+
+   private void sendToQueue(ServerMessage message, Queue queue, Transaction tx) throws Exception {
+      RoutingContext context = new RoutingContextImpl(tx);
+      queue.route(message, context);
+      session.getServer().getPostOffice().processRoute(message, context, false);
+   }
 }
diff --git a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTSessionState.java b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTSessionState.java
index 9458f8b080..31452bfacc 100644
--- a/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTSessionState.java
+++ b/artemis-protocols/artemis-mqtt-protocol/src/main/java/org/apache/activemq/artemis/core/protocol/mqtt/MQTTSessionState.java
@@ -29,14 +29,11 @@ import java.util.concurrent.atomic.AtomicInteger;
 import io.netty.handler.codec.mqtt.MqttTopicSubscription;
 import org.apache.activemq.artemis.api.core.Pair;
 import org.apache.activemq.artemis.core.config.WildcardConfiguration;
-import org.apache.activemq.artemis.core.server.ServerMessage;
 
 public class MQTTSessionState {
 
    private String clientId;
 
-   private ServerMessage willMessage;
-
    private final ConcurrentMap<String, MqttTopicSubscription> subscriptions = new ConcurrentHashMap<>();
 
    // Used to store Packet ID of Publish QoS1 and QoS2 message.  See spec: 4.3.3 QoS 2: Exactly once delivery.  Method B.
@@ -60,7 +57,6 @@ public class MQTTSessionState {
       addressMessageMap.clear();
       pubRec.clear();
       outboundStore.clear();
-      willMessage = null;
    }
 
    OutboundStore getOutboundStore() {
@@ -79,22 +75,6 @@ public class MQTTSessionState {
       this.attached = attached;
    }
 
-   boolean isWill() {
-      return willMessage != null;
-   }
-
-   ServerMessage getWillMessage() {
-      return willMessage;
-   }
-
-   void setWillMessage(ServerMessage willMessage) {
-      this.willMessage = willMessage;
-   }
-
-   void deleteWillMessage() {
-      willMessage = null;
-   }
-
    Collection<MqttTopicSubscription> getSubscriptions() {
       return subscriptions.values();
    }
diff --git a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/mqtt/imported/MQTTTest.java b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/mqtt/imported/MQTTTest.java
index a26a046b2c..7a12f4261d 100644
--- a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/mqtt/imported/MQTTTest.java
+++ b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/mqtt/imported/MQTTTest.java
@@ -37,10 +37,10 @@ import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.TimeUnit;
 import java.util.regex.Pattern;
 
+import org.apache.activemq.artemis.api.core.RoutingType;
 import org.apache.activemq.artemis.api.core.SimpleString;
 import org.apache.activemq.artemis.core.protocol.mqtt.MQTTConnectionManager;
 import org.apache.activemq.artemis.core.protocol.mqtt.MQTTSession;
-import org.apache.activemq.artemis.api.core.RoutingType;
 import org.apache.activemq.artemis.core.server.impl.AddressInfo;
 import org.apache.activemq.artemis.tests.util.Wait;
 import org.fusesource.mqtt.client.BlockingConnection;
@@ -1029,6 +1029,43 @@ public class MQTTTest extends MQTTTestSupport {
       assertEquals("test message", new String(m.getPayload()));
    }
 
+   @Test(timeout = 60 * 1000)
+   public void testWillMessageIsRetained() throws Exception {
+      getServer().createQueue(SimpleString.toSimpleString("will"), RoutingType.MULTICAST, SimpleString.toSimpleString("will"), null, true, false);
+
+      MQTT mqtt = createMQTTConnection("1", false);
+      mqtt.setKeepAlive((short) 1);
+      mqtt.setWillMessage("test message");
+      mqtt.setWillTopic("will");
+      mqtt.setWillQos(QoS.AT_LEAST_ONCE);
+      mqtt.setWillRetain(true);
+
+      final BlockingConnection connection = mqtt.blockingConnection();
+      connection.connect();
+      Wait.waitFor(new Wait.Condition() {
+         @Override
+         public boolean isSatisfied() throws Exception {
+            return connection.isConnected();
+         }
+      });
+
+      // kill transport
+      connection.kill();
+
+      Thread.sleep(10000);
+
+      MQTT mqtt2 = createMQTTConnection("2", false);
+      BlockingConnection connection2 = mqtt2.blockingConnection();
+      connection2.connect();
+      connection2.subscribe(new Topic[]{new Topic("will", QoS.AT_LEAST_ONCE)});
+
+      Message m = connection2.receive(1000, TimeUnit.MILLISECONDS);
+      assertNotNull(m);
+      m.ack();
+      assertEquals("test message", new String(m.getPayload()));
+   }
+
+
    @Test(timeout = 60 * 1000)
    public void testCleanSession() throws Exception {
       final String CLIENTID = "cleansession";