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Project Summary

Project Title: CTF Project | Technical Report on Flag Discovery and Exploitation in a Linux Environment

Platform: TryHackMe

Room: CTF Level One

Author: Athanasios Oikonomopoulos / B4ckD00rR4t

This Capture the Flag (CTF) project was completed as part of the Masterschool cybersecurity program to develop and demonstrate hands-on skills in system exploration, service enumeration, hash cracking, and privilege escalation. The challenge environment, hosted on TryHackMe, featured a vulnerable Linux machine with various misconfigurations and hidden flags.

Throughout the challenge, I:

• Captured 21 flags and credentials, including system, web, hidden, and hash-based flags, by cracking 5 password hashes and extracting 2 ZIP files
• Performed in-depth enumeration and analysis of the file system, services, and web content to uncover vulnerabilities
• Escalated privileges to root by exploiting a misconfigured *sudo* rule on the target system

All findings were documented step-by-step, showing the thought process behind each action, the tools used, and what each discovery revealed about the system's vulnerabilities.

This project validates my ability to conduct system reconnaissance, crack hashes, bypass weak configurations, and escalate privileges in a controlled CTF environment, skills directly transferable to red teaming, SOC analysis, or penetration testing roles.

Whether you’re a fellow learner, a cybersecurity enthusiast, or a hiring manager reviewing this as part of my portfolio, I invite you to follow along through this technical walkthrough. I hope it offers valuable insights, highlights my commitment to continuous growth, and provides a clear look at how I approach challenges in the evolving field of cybersecurity.

Tools I Used