HackTheBox Archetype: A Modern Writeup with AI Guidance on Kali Purple

There is a poetic irony in using the tools that make the internet a chaotic mess to learn how to either defend or exploit its many flaws. As someone who oscillates between technopessimism and a stubborn will to make things work, I recently took on the HackTheBox “Archetype” machine, a classic starting point for those curious about penetration testing. What made this attempt different was my use of Perplexity AI as a real-time assistant, accessed from Firefox on a Kali Purple system. This writeup chronicles my process, the tools and techniques involved, and offers some sardonic commentary on the state of cybersecurity learning.

The journey began with basic setup and enumeration. I used Kali Purple as my base operating system, selected for its curated set of tools and streamlined workflow. Firefox served as my portal to both HackTheBox and Perplexity AI, because memorizing every command is so last decade. OpenVPN connected me to the HackTheBox lab network, putting me on the same subnet as the target machine. I started with a standard nmap scan to enumerate open ports and services. This revealed critical services such as SMB on port 445 and MSSQL on port 1433, setting the stage for further exploitation.

Next, I explored the SMB shares. Using smbclient, I connected to the backups share as an anonymous user. With Perplexity AI at my side, I received step-by-step guidance and explanations, ensuring I did not miss any critical details. I retrieved the prod.dtsConfig file, which contained clear-text credentials for the MSSQL service. This kind of mistake is common in real-world environments, where sensitive data is often left exposed in configuration files.

With the harvested credentials in hand, I moved on to authenticating to the MSSQL server. I used Impacket’s mssqlclient.py to gain access. Once inside, I enabled xp_cmdshell, which allowed me to execute system commands on the host. This demonstrated the dangers of SQL server misconfigurations and the importance of least privilege for service accounts. I used this access to query the system for user information and to search for sensitive files.

The final step was privilege escalation and flag retrieval. By examining the PowerShell history file, I discovered the administrator password. I then used Impacket’s psexec.py to escalate my privileges to Administrator. With a shell as Administrator, I was able to read both the user and root flags. Throughout this process, Perplexity AI helped troubleshoot and refine my commands, especially when transitioning from MSSQL to a full admin shell.

This engagement highlighted the redundancy of tools and techniques available to modern penetration testers. Kali Purple bundles dozens of utilities, many of which overlap in functionality. Open-source projects like Impacket offer multiple ways to achieve the same goal, whether that is SMB access, MSSQL command execution, or privilege escalation. While this abundance is empowering, it also creates a challenge for learners, who must navigate a sea of options and decide which tool to use and when. In my case, Perplexity AI acted as a real-time mentor, helping me make sense of the complexity and suggesting best-practice commands with explanations. This dynamic is emblematic of modern cybersecurity learning, where AI assistants are becoming essential for managing tool sprawl and keeping up with rapidly evolving attack surfaces.

There is a dark humor in all this. The very tools that make the internet fragile are also the ones that help us understand and sometimes exploit its weaknesses. Perhaps the internet needs to be destroyed by its own creations, if only to resolve the contradictions that arise from technological acceleration under capitalism.

Completing the Archetype box with the guidance of Perplexity AI on Kali Purple was both educational and eye-opening. It reinforced the importance of thorough enumeration, the risks of misconfigured services, and the value of having an intelligent assistant to guide you through the ever-growing arsenal of cybersecurity tools. As the field continues to evolve, AI-driven guidance may well become the norm, helping both novices and experts stay sharp and efficient in their craft.

For those curious about Kali Purple’s defensive capabilities, here is a quick overview. The platform includes tools such as Zeek for network monitoring and traffic analysis, Suricata for intrusion detection and prevention, OpenVAS for vulnerability scanning, Kibana for log visualization, Wireshark for protocol analysis, TheHive for incident response, and Kali Autopilot for script automation. These tools, combined with the offensive utilities Kali is known for, make Kali Purple a formidable platform for both breaking and defending networks, a fitting metaphor for the dual nature of modern cybersecurity.

Ready to try your hand at HackTheBox? With the right tools and a little AI guidance, you might just master the art of penetration testing, or at least learn why the internet is doomed.

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