I'm running this in Intellij IDEA, using the IDEA plugin but not yet tried to reproduce outside that.
The plugin lets me select which winstone jar to use. I've been using -lite happily enough, but was going to try using the ReloadingServlet option, so downloaded & switched to the full jar (as that's not in -lite). I found, however that with no other change from -lite other than the jar itself, my config stopped working, with the following error...
[Winstone 2007/09/27 16:35:55] - Error initializing web application: prefix 
[Winstone 2007/09/27 16:35:55] - Winstone Servlet Engine v0.9.9 running: controlPort=disabled
[Winstone 2007/09/27 16:35:55] - HTTP Listener started: port=8080
[Winstone 2007/09/27 16:35:55] - AJP13 Listener started: port=8009
[Winstone 2007/09/27 16:35:55] - Request URL / not found - doesn't match any webapp prefix
If I switch back to -lite, it works and my filter (mapped to "/*" runs fine)