CompTIA PenTest+ Practice Test

What command-line tool allows penetration testers to mask their identity by sending messages through proxy servers?

1. ProxyChains

2. VPN Gateway

3. Tor

4. SSH Tunnel

The correct answer is: ProxyChains

The command-line tool that allows penetration testers to mask their identity by sending messages through proxy servers is ProxyChains. This tool specifically functions by routing connections through a list of proxy servers, effectively anonymizing the traffic and providing additional layers of obfuscation. When using ProxyChains, a penetration tester can specify various types of proxies, including SOCKS and HTTP, creating a chain of proxies that makes it more difficult to trace the source of the traffic. Other tools like VPN Gateway, Tor, and SSH Tunnel are often used for privacy and security in network communications but serve different purposes. A VPN Gateway provides a secure encrypted connection to a private network over the public internet, offering privacy but not necessarily the same level of proxy chaining flexibility as ProxyChains. Tor focuses on anonymity through a decentralized network of volunteer nodes, making it less configurable in terms of specific proxy lists compared to ProxyChains. SSH Tunnel secures data transmission over a secure shell connection, but it typically does not provide the multi-layer proxy capability that ProxyChains does. Thus, ProxyChains is ideally suited for scenarios where detailed control over proxy usage and routing is required.