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Where do I learn about cryptography?
I can recommend "Applied Cryptography" by Bruce Schneier
Not even Bruce Schneier recommends Applied Cryptography. http://www.schneier.com/blog/archives/2009/09/the_cult_of_sc...
Short story: Applied Cryptography is an old book and doesn't focus on end-user practicality. (I'd still recommend it for anyone looking to get deeply into cryptography, but it's not a good starting point.)

For the record, Cryptography Engineering is his latest book on the topic, and it is a good one. But like all technical books, it's also a little out of date.

"Practical Cryptography", by Bruce Schneier and Niels Ferguson, is meant to atone for the unfortunate real-world consequences of Applied Cryptography. It is comprehensive and good for people with basic discrete mathematics understanding.
The Matasano challenges are a good practical starting point to jump right in.

Coursera also has three cryptography classes: Cryptography I, Cryptography II, and Intro to Cryptography (all taught by Dan Boneh).

And, of course, Bruce Schneier's Cryptography Engineering (Applied Engineering is somewhat deprecated).

When I approached this[1] I googled for Python tools for playing with cryptanalysis and found this to be completely irrelevant to what I was trying to do. A small library of NumPy-based functions, on the other hand, did an excellent job.

I don't know how this fares when it comes to blackbox crypto pen-testing, but I must admit I shudder at the thought of blackbox crypto pen-testing.

[1] http://blog.ram.rachum.com/post/56061414423/the-interactive-...