A penetration tester has been given an assignment to attack a series of targets in the 192.168.1.0/24 range, triggering as few alarms and countermeasures as possible. Which of the following Nmap scan syntaxes would BEST accomplish this objective?
D. nmap -sS -O 192.168.1.2/24 -T1
The best Nmap scan syntax to accomplish this objective would be to use the -sS (TCP SYN scan) option, the -O (enable OS detection) option, and the -T1 (timing option) which is the slowest timing option.
The -sS option uses the SYN packet to initiate a connection, which is less likely to be detected by intrusion detection systems (IDS) and firewalls as it does not complete the full TCP connection.
The -O option enables OS detection, which can help identify the type of device that is being scanned and can be useful in identifying vulnerabilities specific to that OS.
The -T1 option sets the timing option to the slowest setting, this will make the scan slower, but also less likely to trigger alarms and countermeasures.
In penetration testing, particularly when you want to be discreet and trigger as few alarms as possible, stealth is key. You would generally want to perform a stealth scan, use a slower timing template to make the scan less obvious, and avoid unnecessary options that could increase visibility.
Among the options provided:
A. Uses TCP connect scan (-sT) and very verbose output (-vvv), and attempts OS detection (-O), which might be more likely to trigger alarms.
B. Scans for service versions (-sV), which is more aggressive and could also trigger alarms.
C. Uses the ACK scan (-sA), which might not be the best choice for stealth in this situation.
D. Uses a SYN stealth scan (-sS), OS detection (-O), and the slowest timing template (-T1), which makes the scan less aggressive and more likely to go undetected.
So, the correct answer is:
D. nmap -sS -O 192.168.1.2/24 -T1
-sS flag not too stealthy these day but I'll go with D
upvoted 5 times
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