
HackTheBox - Fluffy
Source: YouTube · IppSec · published Sep 20, 2025 · 37:38
BLUF: This video walks through the "Fluffy" Hack the Box machine, demonstrating that outdated tools can hinder progress on "easy" boxes due to new vulnerabilities like ESC16, while detailing an initial foothold via a CVE-based SMB exploit 0:00.
Key Takeaways:
• The attacker uses a specially crafted zip file to exploit a Windows SMB vulnerability, triggering an automatic login that captures NTLMv2 hashes for cracking 0:31.
• After cracking credentials, the attacker gains "Service Account Managers" rights, allowing them to add shadow credentials to service accounts for lateral movement 0:29.
• The final privilege escalation relies on the ESC16 vulnerability in ADCS, which requires a recent version of Certipy to detect and exploit the weak security extension mapping 0:07.
Success in modern AD pentesting depends on maintaining updated tooling to identify emerging certificate exploits and leveraging initial footholds for precise privilege escalation paths.
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First 800 characters of the transcript
What's going on YouTube? This is IPS doing Fluffy from Hack the Box, which is an easy assumed breach active directory box. Well, easy as long as you keep your tools up to date as the priv was ADCS ESC16. I know I read off a bunch of letters. That's active directory certificate services escalation number 16. And that's only available in recent versions of Certupy. And these certificate exploits are very hard to find manually. So, if you didn't update Certupy, you're just spinning your wheels for a long time. The box starts off with a set of credentials. You can find a PDF on a fileshare that indicates it's vulnerable to a recent CVE which would cause Windows to make an SMB request upon unzipping a specially crafted zip file. So you create that, upload it to a share get net nm v2 credentials…