Reddit mentions of Windows System Programming (4th Edition) (Addison-Wesley Microsoft Technology Series)

Here is a "curriculum" of sorts I would suggest, as it's fairly close to how I learned:

1. Programming. Definitely learn "C" first as all of the Exploitation and Assembly courses below assume you know C: The bible is pretty much Dennis Richie and Kernighan's "The C Programming Language", and here is the .pdf (this book is from 1988, I don't think anyone would mind). I actually prefer Kochan's book "Programming in C" which is very beginner freindly and was written in 2004 rather than 1988 making the language a little more "up to date" and accessible. There are plenty of "C Programming" tutorials on YouTube that you can use in conjunction with either of the aforementioned books as well. After learning C than you can try out some other languages. I personally suggest Python as it is very beginner friendly and is well documented. Ruby isn't a bad choice either.
   
   
2. Architecture and Computer basics:
   Generally you'll probably want to look into IA-32 and the best starting point is the Intel Architecture manual itself, the .pdf can be found here (pdf link).
   Because of the depth of that .pdf I would suggest using it mainly as a reference guide while studying "Computer Systems: A Programmers Perspective" and "Secrets of Reverse Engineering".
   
   
3. Operating Systems: Choose which you want to dig into: Linux or Windows, and put the effort into one of them, you can come back to the other later. I would probably suggest Linux unless you are planning on specializing in Malware Analysis, in which case I would suggest Windows. Linux: No Starch's "How Linux Works" is a great beginner resource as is their "Linux Command Line" book. I would also check out "Understanding the Linux Kernel" (that's a .pdf link). For Windows you can follow the Windows Programming wiki here or you can buy the book "Windows System Programming". The Windows Internals books are generally highly regarded, I didn't learn from them I use them more as a reference so I an't really speak to how well they would teach a "beginner".
   
   
4. Assembly: You can't do much better than OpenSecurityTraining's "Introductory Intel x86: Architecture, Assembly, Applications, & Alliteration" class lectures from Xeno Kovah, found here. The book "Secrets of Reverse Engineering" has a very beginner friendly introduction to Assembly as does "Hacking: The Art of Exploitation".
   
   
5. Exploitation: OpenSecurityTraining also has a great video series for Introduction to Exploits. "Hacking: The Art of Exploitation" is a really, really good book that is completely self-contained and will walk you through the basics of assembly. The author does introduce you to C and some basic principles of Linux but I would definitely suggest learning the basics of C and Linux command line first as his teaching style is pretty "hard and fast".
   
   
6. Specialized fields such as Cryptology and Malware Analysis.
   
   
   Of course if you just want to do "pentesting/vuln assessment" in which you rely more on toolsets (for example, Nmap>Nessus>Metasploit) structured around a methodology/framework than you may want to look into one of the PACKT books on Kali or backtrack, get familiar with the tools you will use such as Nmap and Wireshark, and learn basic Networking (a simple CompTIA Networking+ book will be a good enough start). I personally did not go this route nor would I recommend it as it generally shys away from the foundations and seems to me to be settling for becoming comfortable with tools that abstract you from the real "meat" of exploitation and all the things that make NetSec great, fun and challenging in the first place. But everyone is different and it's really more of a personal choice. (By the way, I'm not suggesting this is "lame" or anything, it was just not for me.)
   
   *edited a name out
   
   
   
   
   
   

By Johnson M Hart?

Looks like exactly what I need. Thanks.