One of our users, jfgeiger, pointed out that when you begin playing with the new Tomcat settings "antiResourceLocking" and "antiJARLocking" it is possible to get the server into a state where it will ignore newly deployed files from your project to the server even if the "reloadable" property for the context is set to true. So if you are having this problem, try turning off the anti*Locking settings (setting to false) and see if the problem goes away.