diff --git a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionFactoryImpl.java b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionFactoryImpl.java
index b135677d77..47237b5783 100644
--- a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionFactoryImpl.java
+++ b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionFactoryImpl.java
@@ -771,7 +771,11 @@ public class ClientSessionFactoryImpl implements ClientSessionFactoryInternal, C
       ((CoreRemotingConnection) connection).syncIDGeneratorSequence(((CoreRemotingConnection) oldConnection).getIDGeneratorSequence());
 
       for (ClientSessionInternal session : sessionsToFailover) {
-         session.handleFailover(connection, cause);
+         if (!session.handleFailover(connection, cause)) {
+            connection.destroy();
+            this.connection = null;
+            return;
+         }
       }
    }
 
diff --git a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionImpl.java b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionImpl.java
index 55054c4e8b..766ca91bdc 100644
--- a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionImpl.java
+++ b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionImpl.java
@@ -1350,10 +1350,12 @@ public final class ClientSessionImpl implements ClientSessionInternal, FailureLi
    // Needs to be synchronized to prevent issues with occurring concurrently with close()
 
    @Override
-   public void handleFailover(final RemotingConnection backupConnection, ActiveMQException cause) {
+   public boolean handleFailover(final RemotingConnection backupConnection, ActiveMQException cause) {
+      boolean suc = true;
+
       synchronized (this) {
          if (closed) {
-            return;
+            return true;
          }
 
          boolean resetCreditManager = false;
@@ -1426,6 +1428,7 @@ public final class ClientSessionImpl implements ClientSessionInternal, FailureLi
             }
          } catch (Throwable t) {
             ActiveMQClientLogger.LOGGER.failedToHandleFailover(t);
+            suc = false;
          } finally {
             sessionContext.releaseCommunications();
          }
@@ -1448,6 +1451,8 @@ public final class ClientSessionImpl implements ClientSessionInternal, FailureLi
 
       sessionContext.resetMetadata(metaDataToSend);
 
+      return suc;
+
    }
 
    @Override
diff --git a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionInternal.java b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionInternal.java
index 3c6829af7b..a3700b2e50 100644
--- a/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionInternal.java
+++ b/artemis-core-client/src/main/java/org/apache/activemq/artemis/core/client/impl/ClientSessionInternal.java
@@ -66,7 +66,7 @@ public interface ClientSessionInternal extends ClientSession {
 
    void preHandleFailover(RemotingConnection connection);
 
-   void handleFailover(RemotingConnection backupConnection, ActiveMQException cause);
+   boolean handleFailover(RemotingConnection backupConnection, ActiveMQException cause);
 
    RemotingConnection getConnection();
 
diff --git a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/remoting/ReconnectTest.java b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/remoting/ReconnectTest.java
index c2c9f61fab..6eadf4faf2 100644
--- a/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/remoting/ReconnectTest.java
+++ b/tests/integration-tests/src/test/java/org/apache/activemq/artemis/tests/integration/remoting/ReconnectTest.java
@@ -24,6 +24,9 @@ import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicInteger;
 
 import org.apache.activemq.artemis.api.core.ActiveMQException;
+import org.apache.activemq.artemis.api.core.ActiveMQNotConnectedException;
+import org.apache.activemq.artemis.api.core.Interceptor;
+import org.apache.activemq.artemis.api.core.client.ClientSession;
 import org.apache.activemq.artemis.api.core.client.ClientSessionFactory;
 import org.apache.activemq.artemis.api.core.client.FailoverEventListener;
 import org.apache.activemq.artemis.api.core.client.FailoverEventType;
@@ -31,8 +34,11 @@ import org.apache.activemq.artemis.api.core.client.ServerLocator;
 import org.apache.activemq.artemis.api.core.client.SessionFailureListener;
 import org.apache.activemq.artemis.core.client.impl.ClientSessionFactoryInternal;
 import org.apache.activemq.artemis.core.client.impl.ClientSessionInternal;
+import org.apache.activemq.artemis.core.protocol.core.Packet;
+import org.apache.activemq.artemis.core.protocol.core.impl.PacketImpl;
 import org.apache.activemq.artemis.core.server.ActiveMQServer;
 import org.apache.activemq.artemis.core.server.ServerSession;
+import org.apache.activemq.artemis.spi.core.protocol.RemotingConnection;
 import org.apache.activemq.artemis.tests.util.ActiveMQTestBase;
 import org.junit.Assert;
 import org.junit.Test;
@@ -318,6 +324,48 @@ public class ReconnectTest extends ActiveMQTestBase {
 
    }
 
+   @Test
+   public void testReattachTimeout() throws Exception {
+      ActiveMQServer server = createServer(true, true);
+      server.start();
+      // imitate session reattach timeout
+      Interceptor reattachInterceptor = new Interceptor() {
+         @Override
+         public boolean intercept(Packet packet, RemotingConnection connection) throws ActiveMQException {
+            if (packet.getType() == PacketImpl.REATTACH_SESSION) {
+               return false;
+            } else {
+               return true;
+            }
+
+         }
+      };
+      server.getRemotingService().addIncomingInterceptor(reattachInterceptor);
+
+      final long retryInterval = 50;
+      final double retryMultiplier = 1d;
+      final int reconnectAttempts = 10;
+      ServerLocator locator = createFactory(true).setCallTimeout(2000).setRetryInterval(retryInterval).setRetryIntervalMultiplier(retryMultiplier).setReconnectAttempts(reconnectAttempts).setConfirmationWindowSize(-1);
+      ClientSessionFactoryInternal sf = (ClientSessionFactoryInternal) createSessionFactory(locator);
+      final CountDownLatch latch = new CountDownLatch(1);
+      sf.addFailoverListener(eventType -> {
+         if (eventType == FailoverEventType.FAILOVER_FAILED) {
+            latch.countDown();
+         }
+      });
+
+      ClientSession session = sf.createSession(false, true, true);
+      RemotingConnection conn = ((ClientSessionInternal) session).getConnection();
+      conn.fail(new ActiveMQNotConnectedException());
+
+      assertTrue(latch.await(1000, TimeUnit.MILLISECONDS));
+      assertTrue(session.isClosed());
+
+      session.close();
+      sf.close();
+      server.stop();
+   }
+
    // Package protected ---------------------------------------------
 
    // Protected -----------------------------------------------------