Have been looking at the source, although not documented (for TC5.5), it
seems that it is possible to nest a Listener element
(org.apache.catalina.LifecycleListener) under the Server element as 
http://tomcat.apache.org/tomcat-5.5-doc/config/context.html described here
for nesting within Context elements.
This could be used to provide a more elegant way of receiving notification
of when the server has stopped.

However, still not synchronous, looking at JMX for that, seems like I just
need to invoke StandardServer.stop()


Christopher Schultz-2 wrote:
> 
>> Is there a synchronous method for stopping Tomcat, i.e. one that won't
>> return until the ports have been released at least?
> 
> Not that I know of. Lots of folks have posted to the list somewhat
> recently asking basically the same question: how do you know when Tomcat
> has really stopped?
> 
> The best hack I've heard of is to watch the catalina.out log file for
> the magic "Tomcat Stopped" message. Another option would be to actually
> poll the port to see if it's available. They're both pretty ugly options.
> 
> - -chris
> 

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