I Played HackTheBox For 30 Days - Here's What I Learned

Summary

In this 60-day Hack The Box challenge, the user embarks on a journey to master CTF (Capture The Flag) skills by completing a structured series of exercises. Starting with setting up a Kali Linux hacking lab and progressing through beginner-level challenges, the user learns critical tools and techniques like enumeration, exploitation, and privilege escalation. As they tackle real-world-like retired and active machines, the challenge grows in complexity, pushing the user to refine their problem-solving skills. The journey ultimately enhances their confidence in penetration testing, offering valuable hands-on cybersecurity experience.

Takeaways

• 😀 The challenge was designed as a 30-day (extended to 60 days) journey to learn cybersecurity through Hack the Box CTF exercises.
• 😀 Week 1 focused on setting up a hacking lab with Kali Linux and completing 'Starting Point Tier 0' exercises, which introduced basic tools and techniques.
• 😀 The first challenge involved learning how to find 'user' and 'root' flags by exploiting vulnerabilities in virtual machines using open-source tools.
• 😀 Week 2 covered more advanced modules (Starting Point Tier 1 and 2) that explored enumeration, lateral movement, and privilege escalation techniques.
• 😀 The tools covered in Weeks 2 and 3 included nmap, Gobuster, Hashcat, and John the Ripper, with a focus on scanning, web directory enumeration, and password cracking.
• 😀 One key takeaway from the challenge was the importance of understanding the thought process behind exploiting systems and enumerating services to find vulnerabilities.
• 😀 Week 3 introduced retired machines, with the user completing their first retired box, '2 Million,' by exploiting an API for remote code execution.
• 😀 In Week 4, the user tackled active machines like 'Pilgrimage' and 'Cozy Hosting,' applying previously learned techniques like enumeration and privilege escalation.
• 😀 The user found that Hack the Box's structured guides helped provide clarity on methodology, but they wished there was more focus on exploring different attack paths before finding the correct one.
• 😀 The challenge was beneficial for learning real-world penetration testing skills, especially for those in defensive cybersecurity roles, as it provides insights into attacker's methodologies.
• 😀 Despite the challenge taking longer than expected (60 days), the user recommends Hack the Box as a valuable and free resource for anyone interested in improving their pen-testing skills.

Q & A

What was the main goal of the 30-day Hack The Box challenge?

The main goal of the challenge was to improve cybersecurity skills by solving Capture The Flag (CTF) challenges on Hack The Box. This involved learning to use open-source tools, understanding attack methodologies, and discovering vulnerabilities in systems.

What are the key components of the Hack The Box training experience?

The Hack The Box experience is broken down into several key components: setting up a hacking lab, completing 'Starting Point' tiers, progressing through retired and active machines, and applying learned techniques to solve challenges and capture flags.

What tools and techniques were learned during the challenge?

Tools like Nmap, Gobuster, Hashcat, and John the Ripper were used throughout the challenge. Techniques included privilege escalation, SQL injection, local file inclusion, reverse shell creation, and general exploitation of vulnerable services.

What was the significance of 'Starting Point' in Hack The Box?

'Starting Point' is a set of beginner-level exercises in Hack The Box, designed to introduce key penetration testing concepts such as enumeration, exploitation, privilege escalation, and using various attack tools like Nmap and Gobuster.

How did the user feel about the progression of difficulty in Hack The Box?

The user felt that the progression was well-structured. Week 1 was easy and focused on setting up the environment, while Week 2 and Week 3 provided more challenging exercises to learn advanced techniques. Week 4 involved tackling real-world machines with escalating difficulty.

What is the importance of enumeration in penetration testing?

Enumeration is crucial because it helps identify open ports, services, and potential vulnerabilities in a system. It's often the first step in penetration testing and helps attackers understand the system's configuration and weaknesses.

What challenges did the user encounter during the Hack The Box challenge?

The user faced difficulties such as not knowing exactly what to do at first, feeling lost with CTF challenges, and occasionally relying on external write-ups for guidance. However, they found these challenges to be learning opportunities.

Why did the user recommend the Hack The Box challenge despite not completing it within 30 days?

The user recommended the challenge because it provided valuable, hands-on experience in penetration testing. Despite not completing it in 30 days, the user felt that the challenge helped improve their skills and understanding of attack methodologies.

What are some common attack vectors used in the Hack The Box challenges?

Common attack vectors in Hack The Box include SQL injection, exploiting service misconfigurations, using default or weak credentials, and uploading malicious code to spawn reverse shells for gaining remote access.

What was the user’s reflection after completing the challenge?

The user reflected that while the challenge took longer than expected, it was a rewarding experience. It provided hands-on practice with real-world cybersecurity techniques, and the user appreciated the structured learning path from basic to advanced tasks.