You can code up an implementation of 
javax.servlet.http.HttpSessionAttributeListener that tries to serialize each 
attribute when the attributeAdded or attributeReplaced callbacks are called. If 
serialization fails, log the attribute name and the stack trace. Then tweak 
your web.xml to include the listener. Use in dev environment only of course.

I wrote such a thing a while back; it could also descend into collections to 
try to find any offending collection element.  But I can't find it.  Ignoring 
the descending into collections part, it's pretty easy to do, so you could code 
one up.

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