At a minimum you can undeploy your application from asadmin or the console,
and the debugger will still be connected, since it's tied to the container,
not your application. By the same notion, you can attach the debugger to the
server, set breakpoints in your web apps initialization code, and then deploy
the app and the debugger should catch the breakpoints in the your newly
started app. Leaking Threads and ThreadLocals is a common thing that causes
this kind of thing.
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