> Since 5.x, you don't really need to undeploy first, adding update="true" 
> into deploy task will undeploy your app before deployment..

I added that to my Ant script and removed the dependency on
webapp-undeploy. Still works about as often as it doesn't. The WAR
file is removed but the directory isn't - deploy runs and fails
because the path already exists.

This is the Host element in server.xml
<Host name="localhost" appBase="webapps"
       unpackWARs="true" autoDeploy="true"
       xmlValidation="false" xmlNamespaceAware="false">...</Host>

This is the Context element in myWebapp/META-INF/context.xml
<Context antiJARLocking="true" antiResourceLocking="true">...</Context>

Is there any specific logging (Tomcat or system) that I could turn on
to see why the directory isn't always removed on undeploy?

thx
andy

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