diff --git a/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JDBCJournalStorageManager.java b/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JDBCJournalStorageManager.java
index 629405b8a7..9e67f8d900 100644
--- a/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JDBCJournalStorageManager.java
+++ b/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JDBCJournalStorageManager.java
@@ -108,6 +108,8 @@ public class JDBCJournalStorageManager extends JournalStorageManager {
             idGenerator.persistCurrentID();
       }
 
+      deletingLargeMessageTasks.await(30, TimeUnit.SECONDS);
+
       final CountDownLatch latch = new CountDownLatch(1);
       executor.execute(new Runnable() {
          @Override
diff --git a/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManager.java b/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManager.java
index 2ae475c592..df4fec375b 100644
--- a/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManager.java
+++ b/artemis-server/src/main/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManager.java
@@ -65,6 +65,7 @@ import org.apache.activemq.artemis.core.server.LargeServerMessage;
 import org.apache.activemq.artemis.core.server.files.FileStoreMonitor;
 import org.apache.activemq.artemis.journal.ActiveMQJournalBundle;
 import org.apache.activemq.artemis.utils.ExecutorFactory;
+import org.apache.activemq.artemis.utils.ReusableLatch;
 import org.apache.activemq.artemis.utils.critical.CriticalAnalyzer;
 import org.jboss.logging.Logger;
 
@@ -86,6 +87,8 @@ public class JournalStorageManager extends AbstractJournalStorageManager {
 
    protected ReplicationManager replicator;
 
+   protected final ReusableLatch deletingLargeMessageTasks = new ReusableLatch();
+
    public JournalStorageManager(final Configuration config,
                                 final CriticalAnalyzer analyzer,
                                 final ExecutorFactory executorFactory,
@@ -272,6 +275,8 @@ public class JournalStorageManager extends AbstractJournalStorageManager {
             idGenerator.persistCurrentID();
       }
 
+      deletingLargeMessageTasks.await(30, TimeUnit.SECONDS);
+
       final CountDownLatch latch = new CountDownLatch(1);
       try {
          executor.execute(new Runnable() {
@@ -517,6 +522,7 @@ public class JournalStorageManager extends AbstractJournalStorageManager {
 
       };
 
+      deletingLargeMessageTasks.countUp();
       getContext(true).executeOnCompletion(new IOCallback() {
          @Override
          public void done() {
@@ -525,11 +531,13 @@ public class JournalStorageManager extends AbstractJournalStorageManager {
             } else {
                executor.execute(deleteAction);
             }
+
+            deletingLargeMessageTasks.countDown();
          }
 
          @Override
          public void onError(int errorCode, String errorMessage) {
-
+            deletingLargeMessageTasks.countDown();
          }
       });
    }
diff --git a/artemis-server/src/test/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManagerTest.java b/artemis-server/src/test/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManagerTest.java
index a0580941be..4e2741d41e 100644
--- a/artemis-server/src/test/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManagerTest.java
+++ b/artemis-server/src/test/java/org/apache/activemq/artemis/core/persistence/impl/journal/JournalStorageManagerTest.java
@@ -42,6 +42,8 @@ import org.apache.activemq.artemis.core.server.LargeServerMessage;
 import org.apache.activemq.artemis.core.server.impl.JournalLoader;
 import org.apache.activemq.artemis.tests.util.ActiveMQTestBase;
 import org.apache.activemq.artemis.utils.ExecutorFactory;
+import org.apache.activemq.artemis.utils.Wait;
+import org.apache.activemq.artemis.utils.actors.ArtemisExecutor;
 import org.apache.activemq.artemis.utils.actors.OrderedExecutorFactory;
 import org.junit.AfterClass;
 import org.junit.Assert;
@@ -49,6 +51,7 @@ import org.junit.BeforeClass;
 import org.junit.Test;
 import org.junit.runner.RunWith;
 import org.junit.runners.Parameterized;
+import org.mockito.Mockito;
 
 import static java.util.stream.Collectors.toList;
 import static org.hamcrest.Matchers.is;
@@ -212,4 +215,74 @@ public class JournalStorageManagerTest extends ActiveMQTestBase {
       }
    }
 
+   @Test
+   public void testDeletingLargeMessagePendingTasksOnShutdown() throws Exception {
+      if (journalType == JournalType.ASYNCIO) {
+         assumeTrue("AIO is not supported on this platform", AIOSequentialFileFactory.isSupported());
+      }
+      final Configuration configuration = createDefaultInVMConfig().setJournalType(journalType);
+      final ExecutorFactory executorFactory = spy(new OrderedExecutorFactory(executor));
+      final ExecutorFactory ioExecutorFactory = new OrderedExecutorFactory(ioExecutor);
+      final ArtemisExecutor artemisExecutor = executorFactory.getExecutor();
+      final ArtemisExecutor artemisExecutorWrapper = spy(artemisExecutor);
+      Mockito.when(executorFactory.getExecutor()).thenReturn(artemisExecutorWrapper);
+      final JournalStorageManager manager = new JournalStorageManager(configuration, null, executorFactory, null, ioExecutorFactory);
+      manager.start();
+      manager.loadBindingJournal(new ArrayList<>(), new ArrayList<>(), new ArrayList<>());
+      final PostOffice postOffice = mock(PostOffice.class);
+      final JournalLoader journalLoader = mock(JournalLoader.class);
+      manager.loadMessageJournal(postOffice, null, null, null, null, null, null, journalLoader);
+      final LargeServerMessage largeMessage = manager.createLargeMessage(manager.generateID() + 1, new CoreMessage().setDurable(true));
+      final SequentialFile file = largeMessage.getFile();
+
+      boolean fileExists = file.exists();
+      manager.getContext(true).storeLineUp();
+      Assert.assertTrue(fileExists);
+      manager.deleteLargeMessageFile(largeMessage);
+
+      final Thread currentThread = Thread.currentThread();
+      final CountDownLatch beforeLatch = new CountDownLatch(1);
+      final CountDownLatch afterStopLatch = new CountDownLatch(1);
+
+      //Simulate an executor task that begins after store done and ends after manager stop begins.
+      artemisExecutor.execute(() -> {
+         try {
+            //Wait until thread is ready to start executing manager stop.
+            Assert.assertTrue(beforeLatch.await(30000, TimeUnit.MILLISECONDS));
+
+            //Wait until thread executing manager stop is waiting for another thread.
+            Assert.assertTrue(Wait.waitFor(() -> currentThread.getState() == Thread.State.TIMED_WAITING, 30000));
+         } catch (Exception ignore) {
+         }
+      });
+
+      Mockito.doAnswer(invocationOnMock -> {
+         invocationOnMock.callRealMethod();
+
+         if (Thread.currentThread().equals(currentThread) &&
+            invocationOnMock.getArgument(0).getClass().getName().contains(JournalStorageManager.class.getName())) {
+
+            //Simulate an executor task that ends after manager stop.
+            artemisExecutor.execute(() -> {
+               try {
+                  //Wait until manager stop is executed.
+                  afterStopLatch.await(30000, TimeUnit.MILLISECONDS);
+               } catch (Exception ignore) {
+               }
+            });
+         }
+
+         return null;
+      }).when(artemisExecutorWrapper).execute(Mockito.any(Runnable.class));
+
+      manager.getContext(true).done();
+
+      beforeLatch.countDown();
+      manager.stop();
+      fileExists = file.exists();
+      afterStopLatch.countDown();
+
+      Assert.assertFalse(fileExists);
+   }
+
 }