How to Break Web Software
There is a good presentation on Google Video called How To Break Web Software - A look at security vulnerabilities in web software given by Mike Andrews to Google staff. Mike's book also happens to be called How to break web software.
I really liked the session hi-jacking part of the talk, he showed a tool that visualizes the entropy (or randomness) of your session id's. An attacker can then look for weaknesses in the algorithm to guess session id's.
He also does a good job explaining why you should be concerned about XSS.
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