If you put your <Context> fragment in conf/[enginename]/[hostname]/dir1#dir2#appname.xml you can access the webapp via http://[hostname]/dir1/dir2/appname, which I think is what you want. Haven't been able to find this in the Tomcat doc yet, but I did test it successfully on 5.5.9. Have no idea if this trick with the # would work on the name of a .war file.