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I have searched online about this topic and the only information I got is that TCP SYN/ACK can be used to know the type of the target OS. If that is true, I don't understand how this occurs? Does TCP handshaking lead to OS fingerprinting?

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    Have you read OS Detection from nmap? They wrote the book on it. – gowenfawr Apr 17 '16 at 21:56
  • There's also the p0f tool, which can provide some clues/ideas of how such fingerprinting can be done. – Castaglia Apr 17 '16 at 22:14
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OS detection goes a lot further, using all kind of data of the IP and TCP headers fields. If you're into reading, "Silence on the Wire" by Michal Zalewski addresses a lot on this topic.

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