When and how is a java classloader marked for garb

We are creating multiple child classloaders to load in multiple subapplications into a Java application "container", prototyping hot deployment. When the classpath of a particular classloader has changed (i.e. jars have been added, deleted, updated), the old classloader is thrown away (unreferenced) and a new classloader is created for the new classpath of jars.

After updating the classpath, triggering the hot deployment, we took a heap dump. The heap dump (using Memory Analyzer) indicates that the old classloaders were not being garbage collected. Certain classes in the parent classloader were caching the old classloaders. The following things were invoked to clear these caches:

java.lang.ResourceBundle.clearCache(classLoader);
org.apache.commons.logging.LogFactory.release(classLoader);
java.beans.Introspector.flushCaches();

Even after clearing the above caches, the old classloader were still not being garbage collected. The remaining references to the classloader included the following:

the classes loaded by the classloader
java.lang.Package's created by the classloader itself
java.lang.ProtectionDomain created by the classloader itself

All the above are circular references within the classloader, which should trigger a garbage collection. I'm not sure why it is not. Does anybody know why the old classloaders are still not being garbage collected even with the circular references?

I always heard that Classloader unloading was problematic. They are theoretically garbage collected when there is not reference to the object instances and class unloading is not necessary, but in practice it seems like to be more problematic. Subtle references may leak and prevent the Classloader from being reclaimed. In application servers, after numerous redeploy cycle, I sometimes got a OutOfMemoryError: PermGen space.

All that to say that I guess there is a nasty reference somewhere that prevent it from being collected -- maybe the memory analyzer didn't followed the link correctly. It seems like all this can happen, as described in these articles:

Classloader leaks: the dreaded PermGen space exception
How to fix the dreaded PermGen space exception

Also, I don't know exactly what you are doing, but if you can wait for JDK 7, you could have a look at AnonymousClassLoader. They will be introduced to better support dynamic language, as explained in this post: