Index: osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/OSGiContainer.java
===================================================================
--- osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/OSGiContainer.java	(revision 44286)
+++ osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/OSGiContainer.java	(working copy)
@@ -105,12 +105,12 @@
         return shutdown;
     }
 
-    private synchronized void redeploy(Bundle b) throws Exception {
-        if (isShutdown()) return;
+    private synchronized OSGiApplicationInfo redeploy(Bundle b) throws Exception {
+        if (isShutdown()) return null;
         if (isDeployed(b)) {
             undeploy(b);
         }
-        deploy(b);
+        return deploy(b);
     }
 
     /**
@@ -120,26 +120,33 @@
      *
      * @param b Bundle to be deployed.
      */
-    public synchronized void deploy(Bundle b) {
-        if (isShutdown()) return;
+    public synchronized OSGiApplicationInfo deploy(Bundle b) {
+        if (isShutdown()) return null;
+        // By the time this extender is processing the bundle, if the bundle has already changed
+        // state to STOPPING, then cancel the deployment operation.
+        if (b.getState() == Bundle.STOPPING) {
+            logger.logp(Level.INFO, "OSGiContainer", "deploy",
+                    "Bundle {0} is already moved to STOPPING state, so it won't be deployed.", new Object[]{b});
+            return null;
+        }
         OSGiApplicationInfo osgiAppInfo = applications.get(b);
         if (osgiAppInfo != null) {
             logger.logp(Level.WARNING, "OSGiContainer", "deploy",
                     "Bundle {0} is already deployed at {1} ", new Object[]{b,
                             osgiAppInfo.getAppInfo().getSource()});
-            return;
+            return null;
         }
         ServiceReference/*OSGiDeployer*/ osgiDeployerRef = selectDeployer(b);
         if (osgiDeployerRef == null) {
             // No deployer recognises this bundle, so return
-            return;
+            return null;
         }
         OSGiDeployer osgiDeployer = (OSGiDeployer) context.getService(osgiDeployerRef);
         if (osgiDeployer == null) {
             logger.logp(Level.WARNING, "OSGiContainer", "deploy",
                     "Bundle {0} can't be deployed because corresponding deployer {1} has vanished!!!", new Object[]{b,
                             osgiDeployer});
-            return;
+            return null;
         }
 
         // deploy the java ee artifacts
@@ -148,7 +155,7 @@
         } catch (Exception e) {
             logger.logp(Level.WARNING, "OSGiContainer", "deploy",
                     "Failed to deploy bundle " + b, e);
-            return;
+            return null;
         }
         osgiAppInfo.setDeployer(osgiDeployerRef);
         applications.put(b, osgiAppInfo);
@@ -157,6 +164,7 @@
         logger.logp(Level.INFO, "OSGiContainer", "deploy",
                 "deployed bundle {0} at {1}",
                 new Object[]{osgiAppInfo.getBundle(), osgiAppInfo.getAppInfo().getSource().getURI()});
+        return osgiAppInfo;
     }
 
     /**
Index: osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/JavaEEExtender.java
===================================================================
--- osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/JavaEEExtender.java	(revision 44286)
+++ osgi-javaee/osgi-javaee-base/src/main/java/org/glassfish/osgijavaeebase/JavaEEExtender.java	(working copy)
@@ -48,10 +48,8 @@
 import org.osgi.util.tracker.BundleTracker;
 import org.osgi.util.tracker.BundleTrackerCustomizer;
 
-import java.util.concurrent.ExecutionException;
-import java.util.concurrent.ExecutorService;
-import java.util.concurrent.Executors;
-import java.util.concurrent.Future;
+import java.util.Map;
+import java.util.concurrent.*;
 import java.util.logging.Level;
 import java.util.logging.Logger;
 
@@ -103,10 +101,10 @@
         executorService.shutdownNow();
     }
 
-    private synchronized void deploy(Bundle b) {
-        if (!isStarted()) return;
+    private synchronized OSGiApplicationInfo deploy(Bundle b) {
+        if (!isStarted()) return null;
         try {
-            c.deploy(b);
+            return c.deploy(b);
         }
         catch (Exception e) {
             logger.logp(Level.SEVERE, "JavaEEExtender", "deploy",
@@ -115,6 +113,7 @@
             logger.logp(Level.SEVERE, "JavaEEExtender", "deploy",
                     "Exception Stack Trace", e);
         }
+        return null;
     }
 
     private synchronized void undeploy(Bundle b) {
@@ -139,15 +138,20 @@
     }
 
     private class HybridBundleTrackerCustomizer implements BundleTrackerCustomizer {
+        private Map<Long, Future<OSGiApplicationInfo>> deploymentTasks =
+                new ConcurrentHashMap<Long, Future<OSGiApplicationInfo>>();
+
         public Object addingBundle(final Bundle bundle, BundleEvent event) {
             if (!isStarted()) return null;
             final int state = bundle.getState();
             if (isReady(event, state)) {
-                executorService.submit(new Runnable() {
-                    public void run() {
-                        deploy(bundle);
+                Future<OSGiApplicationInfo> future = executorService.submit(new Callable<OSGiApplicationInfo>() {
+                    @Override
+                    public OSGiApplicationInfo call() throws Exception {
+                        return deploy(bundle);
                     }
                 });
+                deploymentTasks.put(bundle.getBundleId(), future);
                 return bundle;
             }
             return null;
@@ -169,13 +173,17 @@
 
         public void removedBundle(final Bundle bundle, BundleEvent event, Object object) {
             if (!isStarted()) return;
-            Future future = executorService.submit(new Runnable() {
-                public void run() {
-                    undeploy(bundle);
+            Future<OSGiApplicationInfo> deploymentTask = deploymentTasks.remove(bundle.getBundleId());
+            if (deploymentTask == null) {
+                // We have never seen this bundle before. Ideally we should never get here.
+                assert(false);
+                return;
+            }
+            try {
+                OSGiApplicationInfo deployedApp = deploymentTask.get();
+                if (deployedApp != null) {
+                    undeploy(bundle); // undeploy synchronously to avoid any deadlock. See GF issue #
                 }
-            });
-            try {
-                future.get();
             } catch (InterruptedException e) {
                 throw new RuntimeException(e); // TODO(Sahoo): Proper Exception Handling
             } catch (ExecutionException e) {