How to learn Assembly

Originally Posted by Nilrem

Can't believe this hasn't been locked yet, well actually it really does all depend on what you mean by the term 'hacking', do you want to learn how to take apart your system and secure it?
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I have two goals here. I come from a UNIX background rather than from the Windows world. I gained much of my success in this world as a sysadmin because I was willing to explore the system at the deepest level available to me. When Linux and its source came out I moved in that direction because I continued to have access to the deepest internals of the system.

Windows is clearly different. The excellent Solomon texts take you a good chunk of the way but they are necessarily limited as to the topics they cover. Understanding what software is doing in the Windows world appears to require looking at disassembled code segments and learning from this what the code is attempting to do. Debuggers, disassemblers, folk lore, and gnostic peerings into a system that is only exposed in that way is not optimum but it appears to be the only way in Windows.

We are a small shop and we are a mixed environment consisting of UNIX (HP-UX, RH AS 2.1 and 3.0 and Windows 2000 server) Because I don't know the Windows stuff well my troubleshooting skills are weak in that world. Frequently I wind up trying to determine where problems might be in a chain that include HP-UX, Oracle, Apache, Forms Server, TCF Framework, network, Windows 2K, IE Explores and Jinitiator. The last 3 pieces are on windows and I just don't know the techniques for getting inside the process and figuring out what happened. Why, for instance, does IE 6 work from a desktop and produce a very strange error when the same laptop is taken home and run through a proxy based security product. Moving backwards to IE 5 solves the problem, but again why????? If you don't know the OS and you can't trace things you will never know. That's just one example.

So by hacking I mean a) understanding of the OS and b) good skills for debug trace and fix.

I was hoping that a checked version of Windows was a compilation of the system with debugging turned on.