diff --git a/hazelcast-client/src/main/java/com/hazelcast/client/connection/nio/ClientConnectionManagerImpl.java b/hazelcast-client/src/main/java/com/hazelcast/client/connection/nio/ClientConnectionManagerImpl.java
index d016989a72241..2f3ac2979f140 100644
--- a/hazelcast-client/src/main/java/com/hazelcast/client/connection/nio/ClientConnectionManagerImpl.java
+++ b/hazelcast-client/src/main/java/com/hazelcast/client/connection/nio/ClientConnectionManagerImpl.java
@@ -19,6 +19,7 @@
 import com.hazelcast.client.AuthenticationException;
 import com.hazelcast.client.ClientExtension;
 import com.hazelcast.client.ClientTypes;
+import com.hazelcast.client.HazelcastClientNotActiveException;
 import com.hazelcast.client.config.ClientConfig;
 import com.hazelcast.client.config.ClientNetworkConfig;
 import com.hazelcast.client.config.ClientProperties;
@@ -63,6 +64,7 @@
 import java.net.InetSocketAddress;
 import java.net.Socket;
 import java.nio.channels.SocketChannel;
+import java.util.Iterator;
 import java.util.Set;
 import java.util.concurrent.ConcurrentHashMap;
 import java.util.concurrent.ConcurrentMap;
@@ -190,6 +192,12 @@ public synchronized void shutdown() {
             connection.close();
         }
         shutdownSelectors();
+        Iterator<AuthenticationFuture> iterator = connectionsInProgress.values().iterator();
+        while (iterator.hasNext()) {
+            AuthenticationFuture future = iterator.next();
+            future.onFailure(new HazelcastClientNotActiveException("Client is shutting down"));
+            iterator.remove();
+        }
         connectionListeners.clear();
         heartbeatListeners.clear();
     }
@@ -288,6 +296,10 @@ private Connection getConnection(Address target, boolean asOwner) {
     }
 
     private AuthenticationFuture triggerConnect(Address target, boolean asOwner) {
+        if (!alive) {
+            throw new HazelcastException("ConnectionManager is not active!!!");
+        }
+
         AuthenticationFuture callback = new AuthenticationFuture();
         AuthenticationFuture firstCallback = connectionsInProgress.putIfAbsent(target, callback);
         if (firstCallback == null) {
@@ -537,7 +549,10 @@ private void authenticated(Address target, ClientConnection connection) {
             fireConnectionAddedEvent(connection);
         }
         assert oldConnection == null || connection.equals(oldConnection);
-        connectionsInProgress.remove(target);
+        if (connectionsInProgress.remove(target) == null) {
+            destroyConnection(connection, new HazelcastClientNotActiveException("Authentication is cancelled"));
+        }
+
     }
 
     private void failed(Address target, ClientConnection connection, Throwable throwable) {
diff --git a/hazelcast-client/src/main/java/com/hazelcast/client/impl/HazelcastClientInstanceImpl.java b/hazelcast-client/src/main/java/com/hazelcast/client/impl/HazelcastClientInstanceImpl.java
index 93abaa1b425f9..c9fdfecdebf55 100644
--- a/hazelcast-client/src/main/java/com/hazelcast/client/impl/HazelcastClientInstanceImpl.java
+++ b/hazelcast-client/src/main/java/com/hazelcast/client/impl/HazelcastClientInstanceImpl.java
@@ -582,11 +582,11 @@ public void shutdown() {
 
     public void doShutdown() {
         proxyManager.destroy();
+        connectionManager.shutdown();
         clusterService.shutdown();
         executionService.shutdown();
         partitionService.stop();
         transactionManager.shutdown();
-        connectionManager.shutdown();
         invocationService.shutdown();
         listenerService.shutdown();
         serializationService.destroy();
diff --git a/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClientInvocationServiceSupport.java b/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClientInvocationServiceSupport.java
index fdc25934c1979..4b739a14ef8d1 100644
--- a/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClientInvocationServiceSupport.java
+++ b/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClientInvocationServiceSupport.java
@@ -168,8 +168,12 @@ public boolean isShutdown() {
     public void shutdown() {
         isShutdown = true;
         responseThread.interrupt();
-        CleanResourcesTask cleanResourcesTask = new CleanResourcesTask();
-        cleanResourcesTask.run();
+        Iterator<ClientInvocation> iterator = callIdMap.values().iterator();
+        while (iterator.hasNext()) {
+            ClientInvocation invocation = iterator.next();
+            iterator.remove();
+            invocation.notifyException(new HazelcastClientNotActiveException("Client is shutting down"));
+        }
         assert callIdMap.isEmpty();
     }
 
@@ -191,8 +195,7 @@ public void run() {
                     continue;
                 }
 
-                int pendingPacketCount = connection.getPendingPacketCount();
-                if (pendingPacketCount != 0) {
+                if (connection.getPendingPacketCount() != 0) {
                     long closedTime = connection.getClosedTime();
                     long elapsed = System.currentTimeMillis() - closedTime;
                     if (elapsed < WAIT_TIME_FOR_PACKETS_TO_BE_CONSUMED_THRESHOLD) {
diff --git a/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClusterListenerSupport.java b/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClusterListenerSupport.java
index e6b543a67306b..fcf1f60b448d0 100644
--- a/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClusterListenerSupport.java
+++ b/hazelcast-client/src/main/java/com/hazelcast/client/spi/impl/ClusterListenerSupport.java
@@ -45,6 +45,7 @@
 import java.util.Set;
 import java.util.concurrent.ExecutorService;
 import java.util.concurrent.Executors;
+import java.util.concurrent.TimeUnit;
 import java.util.logging.Level;
 
 import static com.hazelcast.client.config.ClientProperty.SHUFFLE_MEMBER_LIST;
@@ -52,6 +53,7 @@
 public abstract class ClusterListenerSupport implements ConnectionListener, ConnectionHeartbeatListener, ClientClusterService {
 
     private static final ILogger LOGGER = Logger.getLogger(ClusterListenerSupport.class);
+    private static final long TERMINATE_TIMEOUT_SECONDS = 30;
 
     protected final HazelcastClientInstanceImpl client;
     private final Collection<AddressProvider> addressProviders;
@@ -91,6 +93,15 @@ public Address getOwnerConnectionAddress() {
 
     public void shutdown() {
         clusterExecutor.shutdown();
+        try {
+            boolean success = clusterExecutor.awaitTermination(TERMINATE_TIMEOUT_SECONDS, TimeUnit.SECONDS);
+            if (!success) {
+                LOGGER.warning("cluster executor awaitTermination could not completed in "
+                        + TERMINATE_TIMEOUT_SECONDS + " seconds");
+            }
+        } catch (InterruptedException e) {
+            LOGGER.warning("cluster executor await termination is interrupted", e);
+        }
     }
 
     protected void connectToCluster() throws Exception {
@@ -172,6 +183,12 @@ private void connectToOne() throws Exception {
     private boolean connect(Set<InetSocketAddress> triedAddresses) throws Exception {
         final Collection<InetSocketAddress> socketAddresses = getSocketAddresses();
         for (InetSocketAddress inetSocketAddress : socketAddresses) {
+            if (!client.getLifecycleService().isRunning()) {
+                if (LOGGER.isFinestEnabled()) {
+                    LOGGER.finest("Giving up on retrying to connect to cluster since client is shutdown");
+                }
+                break;
+            }
             try {
                 triedAddresses.add(inetSocketAddress);
                 Address address = new Address(inetSocketAddress);
diff --git a/hazelcast-client/src/test/java/com/hazelcast/client/spi/impl/ClientInvocationTest.java b/hazelcast-client/src/test/java/com/hazelcast/client/spi/impl/ClientInvocationTest.java
index 703ec61dd4839..53ec2108ce687 100644
--- a/hazelcast-client/src/test/java/com/hazelcast/client/spi/impl/ClientInvocationTest.java
+++ b/hazelcast-client/src/test/java/com/hazelcast/client/spi/impl/ClientInvocationTest.java
@@ -138,7 +138,7 @@ public void onResponse(Object response) {
 
                 @Override
                 public void onFailure(Throwable t) {
-                    if (t instanceof HazelcastClientNotActiveException) {
+                    if (t.getCause() instanceof HazelcastClientNotActiveException) {
                         shutdownLatch.countDown();
                     }
                     errorLatch.countDown();