Challenge Overview

You are a part of a penetration testing team that a global supply chain company has retained. The Information Technology department has not cleaned up user-level permissions in over a year. The company wants you to do a security audit of an employee's computer system. The penetration test findings should include data from a specific employee, determine whether the person has unauthorized access to high-level services, and report any results to your superiors. This experience requires skills in network scanning and demonstrates the use of privilege escalation. Knowledge of red team methodologies is essential to this challenge. The target runs on Linux Ubuntu with an IP address of 10.10.1.10. You have user-level SSH access to the machine and your mission is to get root access to the system, find the flag.txt file, and submit the flag value.

What You Will Learn

  • Proper post-exploitation enumeration skills, especially identifying privilege escalation vectors after gaining initial SSH access.
  • Understanding how sudo permissions work in Linux, including how to interpret sudo -l output and detect misconfigured sudo rules.
  • Exploiting misconfigured binaries (GTFOBins techniques) — specifically leveraging awk with elevated privileges to spawn a root shell.
  • Practical knowledge of Linux privilege escalation methodology, including checking PATH, SUID binaries, sudo rights, and system misconfigurations.
  • Applying a structured red team workflow, moving from initial access → enumeration → exploitation → root compromise → flag discovery (flag.txt) on a Linux Ubuntu target (10.10.1.10).

Program Curriculum

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