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My question is: What do I need to know in order to reverse-engineer software on Windows? I have knowledge of Assembly already and now what else I need to learn? Also, can you recommend any book/resource to learn from? (I have found some resources about reversing from The Legend of R4ndom. What do you think about these?)

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Knowledge on assembly is all you really need to get started. To reverse executables on Window learn the Disassembler (IDA) and Debuggers (WinDbg, OllyDbg) as well as the Windows API , if you plan to reverse Windows specific software. Crackmes and keygens are great resource for learning and I would recommend crackme.de, as it contains lots of windows executables.

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