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This is a continuation of a talk I gave at GoGaRuCo 2012 (slides video). The first half of the talk is introducing the concepts of modern cryptography to an audience of Ruby developers. The second half is covering some places where we still commonly screw things up whenever crypto is involved. At GoGaRuCo I was able to cover four pitfalls and take some questions. I had some additional material that I cut to make time, I feel with the extra 15 mins I could cover 2-3 more pitfalls.