I suspect this issue is associated with this bug:
 
 https://issues.apache.org/bugzilla/show_bug.cgi?id=48831

As all shutdown handlers are fired in parallel its possible the logging
handler shutdown hook completes before the Catalina server shutdown hook
resulting in no logging.

** Bug watch added: Apache Software Foundation Bugzilla #48831
   http://issues.apache.org/bugzilla/show_bug.cgi?id=48831

** Also affects: tomcat6 via
   http://issues.apache.org/bugzilla/show_bug.cgi?id=48831
   Importance: Unknown
       Status: Unknown

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https://bugs.launchpad.net/bugs/827922

Title:
  On Tomcat6 shutdown web apps are not able to log anything

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