Any indications in the logs or similar as to why it fails to delete the file?
Windows holding a file lock or something?
the question is very old, but nevertheless ...
I had the same problem with Remote Tomcat.
The solution was ro add "antiJarLocking="true" antiResourceLocking="true"" attributes into the Context element of the context.xml file under CATALINA_HOME/conf. Like this:
<Context antiJarLocking="true" antiResourceLocking="true">