Seconding the recommendation for both of these books. They're both sitting on my desk here and they're both excellent. Tangled Web does a great job of explaining why browser and web app security is in the state that it's in, and each chapter includes a "cheat sheet" at the end of things a developer can do to further secure his web app. Web Application Hacker's Handbook contains exactly what's on the tin: a pretty thorough explanation of how to pull of many of the common exploits, along with the explanation for how/why they work.

While we're talking books and education... tptacek, could you share any resources that you are acquainted with, specifically on the topic of SSL/TLS? I feel a need to really ramp up my knowledge in this space, and would be glad to hear any recommendations you might have.

Note that I'm looking at this from a deployment / administration POV, not programming. I don't want to implement TLS from scratch, just understand the various issues and implications involved in rolling out TLS.

If you have some suggestions, they are much appreciated.