I'm experiencing this problem too with Glassfish v2 and Glassfish v3.
Can I ask you a question: Are you attempting to initialize any persistence object when the application is deployed (through a servlet loaded on startup or a context listener)?
Like bguiz, I've noticed this problem only happens on redeploy. A new deploy to a freshly restarted Glassfish server, never has this problem.
Like FelixM mentioned, I'm convinced this is a class loader issue, however I don't believe it's an issue with multiple wars (I only have 1 deployed to my server). In Glassfish 3, I can see that my WAR is utilizing 2 Glassfish "engines". One for the web(war) and one for the jpa. From what I understand, these are different containers each with their own classloader. I'm guessing Glassfish v2 works in the same manner.
I'm using Spring and (re)initialize some persistence objects on (re)deploy. What I'm thinking, is that while the web engine is reinitializing the war, the jpa engine is still using the old class definitions. Often if I retry the redeploy after this initial failure, it may succeed (sometimes it may take more than one retry but eventually I can get it to succeed without a restart - having better success with Glassfish v3 than v2).
At this point I'm thinking that either these two classloaders are out of sync or there is some sort of race condition on redeploy allowing this operation to sometimes succeed. I've tried to force the classloader, writing code like this
HashMap<Object, Object> properties = new HashMap<Object, Object>();
properties.put(PersistenceUnitProperties.CLASSLOADER, this.getClass().getClassLoader());
entityManagerFactory = Persistence.createEntityManagerFactory(jpaContext, properties);
but it didn't seem to have any affect.
I'm also wondering if eliminating the initialization at startup could fix the problem, giving the appserver time to resynchronize both engines before using any jpa classes (which is why I asked my follow up question).