PEN-200 Port Redirection and Tunneling Practice Question
You are using Proxychains to route your Nmap scan through a SOCKS proxy. Which configuration file must you modify to ensure that the proxy settings are correctly applied during your scan?
⚠ Common exam trap
Candidates often waste time searching for dynamic command-line flags to set proxy details, forgetting that Proxychains relies entirely on editing a static local configuration file.
Answer choices
Why each option matters
Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
✓
/etc/proxychains.conf
Proxychains relies on a configuration file to determine which proxy servers to use for traffic redirection. Misconfiguring this file is a common pitfall that leads to scans either failing or leaking traffic directly from your machine. Correctly setting the proxy type, IP address, and port ensures that all traffic generated by the tools you prefix with proxychains is routed through the specified tunnel, maintaining your stealth and reachability.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
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/etc/nmap/nmap.conf
Why it's wrong here
This file is for Nmap-specific configurations, such as default scripts or NSE library paths. It has no influence on how tools are proxied at the network layer. Modifying this will not affect the routing of packets, as it does not interact with the Proxychains daemon or its library interposition mechanism.
- ✓
/etc/proxychains.conf
Why this is correct
This is the default configuration file for Proxychains. It defines the proxy servers, the chain type, and other operational parameters. Editing this file to add your SOCKS proxy entry at the bottom is the standard procedure to enable Proxychains to successfully route traffic through your established pivot tunnel.
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/etc/ssh/ssh_config
Why it's wrong here
The ssh_config file manages client-side SSH behavior, such as timeouts and identity files. While it can be used for local port forwarding via SSH, it does not control the Proxychains utility. Configuring this will not affect how Proxychains routes traffic for other tools like Nmap or Metasploit modules.
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/etc/network/interfaces
Why it's wrong here
This file manages the local system's physical and virtual network interfaces. It is used for configuring IP addresses, gateways, and netmasks for the host itself. It has no role in application-layer proxying or the redirection of traffic for tools running within the user space, making it irrelevant for this task.
About these practice questions
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JA
Written and reviewed by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
Last reviewed September 2026 · checked against the official OffSec exam blueprint
This PEN-200 practice question is part of Courseiva's free OffSec certification practice question bank. Courseiva provides original exam-style practice questions with explanations, topic-based practice, mock exams, readiness tracking, and study analytics to help learners prepare for the PEN-200 exam.