This review comes almost a year late for a mate of mine extracted a blood oath to write a review on this book. My apologies for taking so long.
"Grey Hat Python", written by Justin Seitz, a Senior Security Researcher at Immunity Inc, is a book which takes you through the process of reverse engineering using the Python language. He talks about automating simple tasks, writing fuzzers, debuggers, how to create your own hooks (soft and hard), sniffers and more. Does this book live up to its namesake? Overall yes, although I will say not without some disappointments- although not all are the author's fault.
Firstly, the book suffers from a timing issue. It was released in 2009, around the same time as Windows 7 and new versions of Python (2.6 and 3.0 released relatively close together). The first issue is substantial as the author assumes that the reader is working in a purely 32bit environment. Now I know that a lot of developers that do, but I think this is a dangerous assumption given that 64 bit operating systems were not new and beginning with Windows 7 (with a much wider adoption than vista) a lot more prevalent. The second is arguably forgivable, given readers could use Python 2.6 without too much issue (although older Python functions might cause grief).
With that said, the book wastes no time deep diving into the process by getting the author to explain how to setup your development environment and gives some Pythonic basics (e.g. explaining data types as they exist in Python when compared to C) and before long writing basic Python loops, delving into Assembly language and debugging basics. As you can imagine, this is not a book for programming noobs and you should have at least one language (the author assumes you have C at a minimum) under your belt before you trying this book, preferrably some Python know how. If you want a good book to learn Python, I'm a fan of Zed A. Shaw's "Learn Python The Hard Way" and the Python doco online when you hit his deliberate mistakes and trick questions.
One criticism I read about this book elsewhere is how that it is a massive pitch for the Immunity Debugger. Firstly, I think this is an unfair criticism. The tool is widely used by security researchers around the world. I admit it isn't the only one but even with Dave Aitel's introduction, it is made quite clear that Immunity have chosen to standardise on the same language and same tools to better facilitate teamwork, automation and code re-use. Knowing who Immunity are and their reputation within the industry, you cannot really argue with their results. If you take that onboard, then you accept that you're learning from masters of their craft and they are trying to instill in you their work practices and techniques, not just code. The author is aiming to teach you the process and how to optimise it. In that respect, I felt this is much more valuable and that the book certainly achieved its aims in giving you and overview of the basics of research engineering and security research.
Two areas I felt the book could have covered better was ASLR and how this affects exploit development. Firstly, I'm currently reading "The Art of Software Security Assessment" and that book was written in 2004 and touches on ASLR. Being 2009, this book specifically touches on DEP but doesn't even mention ASLR. I feel that completely skipping ASLR is a fairly unforgivable mistake. I realise this complicates the entire process but even a single paragraph explaining "No I'm not covering this and here's why" would have been better. If nothing else, the book could have stated "I will be touching upon these items in my sequel", promising to delve further into more advanced techniques and scenarios (ROP gadgets, heap spraying, sandbox bypasses, etc). Secondly, I felt the lack of any reference to 64 bit processors was also an oversight. I suspect the author began writing this book sometime prior to the 2009 release and subsequently this is what gives this book a somewhat dated feel.
Taking all that aside, the author's style is simple, easy to follow and the book well structured logically. Each chapter seemlessly flows into the next and the coding examples seemed simple enough (I'd only gone through a few chapters, certainly not all of them so I cannot state for certain that the book contains no errors). This book is quite light at 181 pages (ignoring the Index) and definitely one of the lighter reads. Although for the price ($39.95 USD) I do feel it is on the steeper side given the above issues. If you're relatively new to security research and reversing however (which is clearly the target audience), then it's probably still worth it. Being honest, these areas are not my forte so the book felt "just right" for me. Take that for what you will. If you spend all day reversing then you will find this book far too light. I should also probably point out that I didn't pay money for this book, it was a gift from our good friends at O'Reilly via. my local OWASP chapter so I have no right to complain. :)
Would I still recommend this book? Absolutely. I would also be amoung the first that would buy an updated edition or a sequel. I can certainly hope Justin Seitz writes another book (both a sequel and new edition would be great!). He has a great writing style and I think has a promising future ahead of him as a technical writer. I hope he continues to write books on this topic and explores it more fully.
Overall rating? 4 out of 5.