Stop Apache Tomcat when web application stops

Scenario:

Apache Tomcat 6.0 is started as a service on Windows Server 2008 R2 using a wrapper (org.tanukisoftware.wrapper.WrapperStartStop) which uses org.apache.catalina.startup.Bootstrap. In course of the Tomcat startup one web application is also started. This web application needs to connect to a remote database and check the connection. It retries to connect a couple of times if the database is not available and then shutdown after x tries.

Problem:

I need to stop Apache Tomcat after the web app exits when the database connection is not available.

Possible solutions:

• Stop Apache Tomcat from within the web application (already tried the shutdown port which did not work because the connection was refused - with a standalone Java application it worked)
• Call an external Java application from within the web application
• Configure Apache Tomcat to shut down if the only web application shuts down - I could not find a way to do that

Any ideas? Maybe a different approach?

System.exit(0) from within your webapp will shut down the Tomcat instance if there is no security manager configured.

Works from a standalone server, not sure whether it works when running as a Windows service.

Edit: though you might want to read this: Calling System.exit() in Servlet's destroy() method