Really cool the Matasano Crypto Challenges is "a collection of 48 exercises that demonstrate attacks on real-world crypto."
It's designed to teach real Crypto attacks by doing, great for improving the security of code you write, or to get an idea of what Pen Testing or malicious hacking involves.
Very good review, worth reading in it's own right here https://blog.pinboard.in/2013/04/the_matasano_crypto_challenges/
Note in the Pinboard review the original link for Matasano Crypto Challenges didn't update for server move, current working link (I have correct link at top of this blog post of mine as well) is http://web.archive.org/web/20140213141638/http://www.matasano.com/articles/crypto-challenges/
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