Index: tomcat/src/main/java/org/jboss/web/tomcat/service/deployers/TomcatDeployment.java
===================================================================
--- tomcat/src/main/java/org/jboss/web/tomcat/service/deployers/TomcatDeployment.java	(revision 111633)
+++ tomcat/src/main/java/org/jboss/web/tomcat/service/deployers/TomcatDeployment.java	(working copy)
@@ -37,6 +37,8 @@
 import javax.management.MBeanServer;
 import javax.management.ObjectName;
 import javax.naming.Context;
+import javax.naming.InitialContext;
+import javax.naming.NamingException;
 
 import org.apache.catalina.Container;
 import org.apache.catalina.Engine;
@@ -380,6 +382,10 @@
 
       public void lifecycleEvent(LifecycleEvent event)
       {
+          if(event.getType().equals(StandardContext.DESTROY_EVENT))
+          {
+              unbindSecurityDomainJndiBindings(webApp);
+          }
 
          if (event.getType().equals(StandardContext.AFTER_START_EVENT))
          {
@@ -455,6 +461,36 @@
          }
       }
 
+      private void unbindSecurityDomainJndiBindings(WebApplication webApplication) 
+      {
+           InitialContext initialContext = null;
+           Thread currentThread = Thread.currentThread();
+           ClassLoader currentLoader = currentThread.getContextClassLoader();
+           try 
+           {
+               currentThread.setContextClassLoader(webApplication.getMetaData().getENCLoader());
+               initialContext = new InitialContext();
+               final Context envCtx = (Context) initialContext.lookup("java:comp");
+               unlinkSecurityDomain(webApplication.getMetaData().getSecurityDomain(), envCtx);
+           } catch (final NamingException e)
+           {
+               log.error(e.getMessage(), e);
+           }
+           finally 
+           {
+               if (initialContext != null)
+               {
+                   try
+                   {
+                       initialContext.close();
+                   } catch (final NamingException ignore)
+                   {
+                       log.warn(ignore.getMessage(), ignore);
+                   }
+               }
+               currentThread.setContextClassLoader(currentLoader);
+           }
+       }
    }
 
    public Loader getWebLoader(DeploymentUnit unit, JBossWebMetaData metaData, ClassLoader loader, URL rl, TomcatInjectionContainer injectionContainer) throws MalformedURLException
@@ -524,7 +560,6 @@
          }
       }
       performUndeployInternal(warInfo, hostName, warUrl);
-
    }
 
    protected void performUndeployInternal(WebApplication warInfo, String hostName, String warUrlStr) throws Exception
Index: server/src/main/java/org/jboss/web/deployers/AbstractWarDeployment.java
===================================================================
--- server/src/main/java/org/jboss/web/deployers/AbstractWarDeployment.java	(revision 111633)
+++ server/src/main/java/org/jboss/web/deployers/AbstractWarDeployment.java	(working copy)
@@ -839,6 +839,16 @@
       Util.bind(javaCompCtx, "env/security/security-domain", new LinkRef(securityDomain));
       Util.bind(javaCompCtx, "env/security/subject", new LinkRef(securityDomain + "/subject"));
    }
+   
+   protected void unlinkSecurityDomain(String securityDomain, Context javaCompCtx) throws NamingException
+   {
+      log.debug("UnLinking security/securityMgr from JNDI ");
+      Util.unbind(javaCompCtx, "env/security/securityMgr");
+      Util.unbind(javaCompCtx, "env/security/realmMapping");
+      Util.unbind(javaCompCtx, "env/security/authorizationMgr");
+      Util.unbind(javaCompCtx, "env/security/security-domain");
+      Util.unbind(javaCompCtx, "env/security/subject");
+   }
 
    /**
     * A utility method that searches the given loader for the resources: