Nick, you state that some jar files cannot be deleted.  Is that because they 
are in use?  If so, the most likely cause is that the app server is holding on 
to session information for sessions that have not yet timed out.

Try this.  Set the session-timeout in web.xml to a low number, like 1.  Then 
deploy the the web.xml file.  This should cause JBoss to redeploy the app.  
Wait about 5 seconds (the default time used by hot-deploy, adjust if you 
changed that time), and then try deleting the directory.  Try it by hand first, 
and if it works, it should be fairly simple to teach ant how to do this.

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