diff --git a/artemis-protocols/artemis-amqp-protocol/src/main/java/org/apache/activemq/artemis/protocol/amqp/broker/AMQPMessage.java b/artemis-protocols/artemis-amqp-protocol/src/main/java/org/apache/activemq/artemis/protocol/amqp/broker/AMQPMessage.java
index 0bcf57257f..6c9e6fb9fb 100644
--- a/artemis-protocols/artemis-amqp-protocol/src/main/java/org/apache/activemq/artemis/protocol/amqp/broker/AMQPMessage.java
+++ b/artemis-protocols/artemis-amqp-protocol/src/main/java/org/apache/activemq/artemis/protocol/amqp/broker/AMQPMessage.java
@@ -524,7 +524,11 @@ public abstract class AMQPMessage extends RefCountMessage implements org.apache.
    }
 
    protected Object getMessageAnnotation(String annotation) {
-      return getMessageAnnotation(Symbol.getSymbol(annotation));
+      Object messageAnnotation = getMessageAnnotation(Symbol.getSymbol(AMQPMessageSupport.toAnnotationName(annotation)));
+      if (messageAnnotation == null) {
+         messageAnnotation = getMessageAnnotation(Symbol.getSymbol(annotation));
+      }
+      return messageAnnotation;
    }
 
    protected Object getMessageAnnotation(Symbol annotation) {
diff --git a/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/Queue.java b/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/Queue.java
index eb04963c4d..628e43e1f0 100644
--- a/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/Queue.java
+++ b/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/Queue.java
@@ -361,6 +361,10 @@ public interface Queue extends Bindable,CriticalComponent {
 
    int retryMessages(Filter filter) throws Exception;
 
+   default int retryMessages(Filter filter, Integer expectedHits) throws Exception {
+      return retryMessages(filter);
+   }
+
    void addRedistributor(long delay);
 
    void cancelRedistributor() throws Exception;
diff --git a/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/impl/QueueImpl.java b/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/impl/QueueImpl.java
index ef0abf2293..2379d5e648 100644
--- a/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/impl/QueueImpl.java
+++ b/artemis-server/src/main/java/org/apache/activemq/artemis/core/server/impl/QueueImpl.java
@@ -2140,6 +2140,7 @@ public class QueueImpl extends CriticalComponentImpl implements Queue {
                                       QueueIterateAction messageAction) throws Exception {
       int count = 0;
       int txCount = 0;
+      Integer expectedHits = messageAction.expectedHits();
       // This is to avoid scheduling depaging while iterQueue is happening
       // this should minimize the use of the paged executor.
       depagePending = true;
@@ -2170,6 +2171,9 @@ public class QueueImpl extends CriticalComponentImpl implements Queue {
                      }
                      txCount++;
                      count++;
+                     if (expectedHits != null && count >= expectedHits.intValue()) {
+                        break;
+                     }
                   }
                }
 
@@ -2611,10 +2615,20 @@ public class QueueImpl extends CriticalComponentImpl implements Queue {
 
    @Override
    public int retryMessages(Filter filter) throws Exception {
+      return retryMessages(filter, null);
+   }
+
+   @Override
+   public int retryMessages(Filter filter, Integer expectedHits) throws Exception {
 
       final HashMap<String, Long> queues = new HashMap<>();
 
       return iterQueue(DEFAULT_FLUSH_LIMIT, filter, new QueueIterateAction() {
+         @Override
+         public Integer expectedHits() {
+            return expectedHits;
+         }
+
          @Override
          public boolean actMessage(Transaction tx, MessageReference ref) throws Exception {
 
@@ -4164,6 +4178,10 @@ public class QueueImpl extends CriticalComponentImpl implements Queue {
     */
    abstract class QueueIterateAction {
 
+      public Integer expectedHits() {
+         return null;
+      }
+
       /**
        *
        * @param tx   the transaction which the message action should participate in
diff --git a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/amqp/AmqpExpiredMessageTest.java b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/amqp/AmqpExpiredMessageTest.java
index 30b3f7a408..38d324f6ac 100644
--- a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/amqp/AmqpExpiredMessageTest.java
+++ b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/amqp/AmqpExpiredMessageTest.java
@@ -128,6 +128,52 @@ public class AmqpExpiredMessageTest extends AmqpClientTestSupport {
       connection.close();
    }
 
+   @Test(timeout = 60000)
+   public void testRetryExpiry() throws Exception {
+      AmqpClient client = createAmqpClient();
+      AmqpConnection connection = addConnection(client.connect());
+      AmqpSession session = connection.createSession();
+
+      AmqpSender sender = session.createSender(getQueueName());
+
+      // Get the Queue View early to avoid racing the delivery.
+      final Queue queueView = getProxyToQueue(getQueueName());
+      assertNotNull(queueView);
+
+      AmqpMessage message = new AmqpMessage();
+      message.setTimeToLive(1);
+      message.setText("Test-Message");
+      message.setDurable(true);
+      message.setApplicationProperty("key1", "Value1");
+      sender.send(message);
+
+      message = new AmqpMessage();
+      message.setTimeToLive(1);
+      message.setBytes(new byte[500 * 1024]);
+      sender.send(message);
+      sender.close();
+
+      final Queue dlqView = getProxyToQueue(getDeadLetterAddress());
+
+      Wait.assertEquals(2, dlqView::getMessageCount);
+      Assert.assertEquals(2, dlqView.retryMessages(null));
+      Wait.assertEquals(0, dlqView::getMessageCount);
+      Wait.assertEquals(2, queueView::getMessageCount);
+
+
+      AmqpReceiver receiver = session.createReceiver(getQueueName());
+      // Now try and get the message
+      receiver.flow(2);
+      for (int i = 0; i < 2; i++) {
+         AmqpMessage received = receiver.receive(5, TimeUnit.SECONDS);
+         assertNotNull(received);
+         received.accept();
+      }
+      connection.close();
+      Wait.assertEquals(0, queueView::getMessageCount);
+      Wait.assertEquals(0, dlqView::getMessageCount);
+   }
+
    /** This test is validating a broker feature where the message copy through the DLQ will receive an annotation.
     *  It is also testing filter on that annotation. */
    @Test(timeout = 60000)