Oh... you're kidding, right?
Well, the context is actually an acronym which is why it was created uppercase but I know the users are going to mess up the url and type it in lowercase which will get them absolutely nowhere.
I find it a little strange that it is Tomcat that throws the 404 when accessing the lowercase context (e.g.
http://myserver.com/test) and not IIS (since Tomcat is only configured for the uppercase url).