Looking at the logs added to
https://issues.apache.org/bugzilla/show_bug.cgi?id=54315, the undeploy
log in the failure case is a lot shorter. The Context appears to have no
children (not even the servlets picked up from the default web.xml)
which indicates that the deployment failed.

My best guess at this point remains that the trigger for things going
wrong is that an undeployment fails, possibly with a locked file.

I'd suggest the following to progress this:
1. Look further back in the logs for when things first went wrong.

2. Try Tomcat 8 and enable trackLockedFiles (see
http://tomcat.apache.org/tomcat-8.0-doc/config/resources.html )

Mark

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