> TRIPLA SECURITY

Summary

1. Introduction
2. Content Overview
3. My Experience
4. Quick Tricks & Tools
5. Conclusion

1. Introduction

The Zephyr Pro Lab on Hack The Box offers an engaging and hands-on experience for intermediate-level users who want to level up their skills in Active Directory exploitation and red teaming. This lab simulates a real corporate environment filled with common security flaws and misconfigurations that you might encounter in the wild. It’s a great chance to hone your abilities in OSINT, phishing, privilege escalation, and lateral movement, all while facing a variety of challenges. Your goal is to escalate your privileges to Domain Admin and collect all the flags hidden across the lab. With 17 machines spread across the network, each offering its own set of challenges.

2. Content Overview

Zephyr consists of a series of challenges primarily based on Active Directory misconfigurations, privilege escalation paths, and lateral movement techniques. These core concepts are essential for penetration testers looking to improve their red teaming skills, particularly in a Windows environment. However, the lab also includes Linux machines and web applications, which provide a break from the Windows centric challenges and offer different attack vectors.

While the Linux machines and web applications are relatively easier to hack, the Active Directory and Windows based machines pose more of a challenge, with each machine requiring a different approach. The difficulty increases as you progress through the lab, especially in terms of the complexity of the attacks you need to perform and the enumeration required.

By the end of the lab, you will not only apply your existing knowledge of Active Directory pentesting, but you’ll also gain valuable experience from the attacks that don’t go as planned. This forces you to think critically and adapt your approach, which is a key skill for real-world engagements. Throughout the lab, you’ll hone the following skills and be able to perform them proficiently:

• Enumeration
• Exploitation of Active Directory flaws
• Relay attacks
• Lateral movement
• Privilege escalation
• Pivoting
• SQL attacks
• Password cracking
• Web application attacks

3. My Experience

The Zephyr Pro Lab can be finished in a few days if you’re fully dedicated, but for me, it took about 14 days, spending 3/4 hours each day. Sometimes I struggled to make progress because I couldn’t exploit a machine, but that’s just part of the learning process. The time you spend will vary depending on your approach.

My advice is to really focus on properly enumerating each machine. Sometimes the solution is simple, but you might miss it if you don’t do thorough enumeration. Also, make sure to practice pivoting and maintaining persistence on compromised machines, as they can lose connection after a while. Make sure you’ve set everything up properly for a fresh start on each machine. A few machines will also require AV bypass, so do some research online, there are plenty of resources to help you with that.

4. Quick Tricks & Tools

If you’re looking for some useful tools to help you in your journey through the lab, here’s a great GitHub repository that contains a collection of pre-compiled .NET binaries and other executables specifically designed for penetration testing in Windows Active Directory environments. This will save you time on getting the right tools: https://github.com/jakobfriedl/precompiled-binaries?tab=readme-ov-file

• BloodHound: A powerful AD enumeration tool that helps you map attack paths and understand relationships between objects in Active Directory, making your attack planning easier.
• CrackMapExec / Netexec: Tools for automating post-exploitation tasks. Netexec is a solid alternative to CrackMapExec with even better features. Full collection here: https://www.netexec.wiki/
• Mimikatz: A well-known tool for extracting passwords, Kerberos tickets, and other sensitive data from Windows machines, ideal for privilege escalation.
• Rubeus: A tool for interacting with Kerberos tickets useful for requesting, renewing, and forging tickets to exploit Kerberos based systems.
• Ligolo-ng: A great tool for pivoting and bypassing network barriers to move between machines.
• Metasploit: I don’t think I need to explain this one much it’s pretty well known. Metasploit helps with exploiting vulnerabilities and launching payloads. It’s a must have in any pentesting toolkit.

A few extra tips: Sometimes, when you’re stuck, don’t hesitate to search for solutions on Google or YouTube. There’s a lot of valuable information out there. Also, take notes of everything you discover during the lab: credentials, domain names, or any other small detail might be crucial later on when you’re nearing the end of the lab. It’s all about using the clues you find at the right time.

5. Conclusion

The Zephyr Pro Lab on Hack The Box is a fun and challenging way to level up your skills in Active Directory and red teaming. It’s packed with real world flaws and misconfigurations, giving you plenty of opportunities to practice your hacking skills. While it can be tough at times, the lessons you learn are super valuable. From figuring out how to escalate privileges to mastering pivoting and persistence, the lab covers it all.

Overall, Zephyr is a great lab for anyone looking to improve their AD pentesting abilities. It might take some time and effort, but by the end, you’ll feel more confident in your skills. Remember, the learning never stops!