I've been butting my head against this problem while deploying and undeploying a complex web application too, and thought I'd add an explanation and my solution.
When I deploy an application on Apache Tomcat, a new ClassLoader is created for that app. The ClassLoader is then used to load all the application's classes, and on undeploy, everything's supposed to go away nicely. However, in reality it's not quite as simple.
One or more of the classes created during the web application's life holds a static reference which, somewhere along the line, references the ClassLoader. As the reference is originally static, no amount of garbage collecting will clean this reference up - the ClassLoader, and all the classes it's loaded, are here to stay.
And after a couple of redeploys, we encounter the OutOfMemoryError.
Now this has become a fairly serious problem. I could make sure that Tomcat is restarted after each redeploy, but that takes down the entire server, rather than just the application being redeployed, which is often not feasible.
So instead I've put together a solution in code, which works on Apache Tomcat 6.0. I've not tested on any other application servers, and must stress that this is very likely not to work without modification on any other application server.
I'd also like to say that personally I hate this code, and that nobody should be using this as a "quick fix" if the existing code can be changed to use proper shutdown and cleanup methods. The only time this should be used is if there's an external library your code is dependent on (In my case, it was a RADIUS client) that doesn't provide a means to clean up its own static references.
Anyway, on with the code. This should be called at the point where the application is undeploying - such as a servlet's destroy method or (the better approach) a ServletContextListener's contextDestroyed method.
//Get a list of all classes loaded by the current webapp classloader
WebappClassLoader classLoader = (WebappClassLoader) getClass().getClassLoader();
Field classLoaderClassesField = null;
Class clazz = WebappClassLoader.class;
while (classLoaderClassesField == null && clazz != null) {
try {
classLoaderClassesField = clazz.getDeclaredField("classes");
} catch (Exception exception) {
//do nothing
}
clazz = clazz.getSuperclass();
}
classLoaderClassesField.setAccessible(true);
List classes = new ArrayList((Vector)classLoaderClassesField.get(classLoader));
for (Object o : classes) {
Class c = (Class)o;
//Make sure you identify only the packages that are holding references to the classloader.
//Allowing this code to clear all static references will result in all sorts
//of horrible things (like java segfaulting).
if (c.getName().startsWith("com.whatever")) {
//Kill any static references within all these classes.
for (Field f : c.getDeclaredFields()) {
if (Modifier.isStatic(f.getModifiers())
&& !Modifier.isFinal(f.getModifiers())
&& !f.getType().isPrimitive()) {
try {
f.setAccessible(true);
f.set(null, null);
} catch (Exception exception) {
//Log the exception
}
}
}
}
}
classes.clear();