I thought Reloadable set to true will only work for JSPs? Will that
allow classes to be reloaded as well ?
What would trigger that?

Hmm .. I may be delerious, but I feel like when reloadable="true", the context gets reloaded whenever something 'changes' in the WEB-INF dir .. let's see ...

got this from the docs:
http://jakarta.apache.org/tomcat/tomcat-4.1-doc/config/context.html
(Tomcat 4, but I'm a bit lazy to go to tommcat 5, and I can't imagine it 
changing too much)

reloadable:

Set to true if you want Catalina to monitor classes in /WEB-INF/classes/ and 
/WEB-INF/lib for changes, and automatically reload the web application if a 
change is detected. This feature is very useful during application development, 
but it requires significant runtime overhead and is not recommended for use on 
deployed production applications. You can use the Manager web application, 
however, to trigger reloads of deployed applications on demand.

I figured I had to find a way to programmatically make tomcat restart
the web app. No idea how yet, other than writing to web.xml to modify it
or looking into tomcat API .

Hmm .. nothing ingenious .. what if use some lo-tech style of a shell script that justs request the correct url to reload a particular webapp context ...

The Eclipse sysdeo plugin has a way of telling a context to reload ... might be 
something to look into.

-steve

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