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The king of the stack fingerprinting programs today is nmap. I had often wondered exactly how Fyodor, the author of nmap, went about designing his program. In his paper, Fyodor mentions TCP options, and how useful these options are for OS identification via stack fingerprinting, and this column goes deeper into TCP options, and how they are used by TCP/IP, and nmap.
The link for this article located at Spirit.com / Rik Farrow is no longer available.