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Security Warrior by Anton Chuvakin, Cyrus Peikari

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Chapter 9. OS Fingerprinting

OS fingerprinting is the science of determining the operating systems in use on a remote network. Fingerprinting is one of the first steps in an attack. Most vulnerabilities are dependent on the target OS, so fingerprinting is a vital skill. Although you can never fingerprint with 100% accuracy, the science is evolving to approach that level.

When might you need OS fingerprinting? If a remote company hires you to perform vulnerability testing, it is better if they do not provide you with detailed knowledge of their network. Before taking a company tour to inspect their security architecture, the first phase of any security audit should be a “blind” intrusion attempt from the Internet. You start the way an attacker does: gathering information on an occult target before attacking. This also applies when doing an audit of your own networks. In this chapter, we demonstrate simple and advanced techniques for OS fingerprinting. We also show technologies that have automated the fingerprinting process, including the tools Nmap, p0f, Xprobe, and RING.

Telnet Session Negotiation

Telnet session negotiation (TSN) is the simplest way to determine a remote OS. All it requires is that you telnet to the server. It is surprising how many systems have telnet running for no reason. Worse, many networks respond with a banner that gives the exact OS version! Although this method is not elegant, it is nevertheless effective. TSN should be the first thing you check in fingerprinting. ...

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