Tentacle

Verified writeups for the Tentacle machine of Hack The Box

Tentacle

$ tldr Squid + WPAD → OpenSMTPD exploit → Kerberos SSH + .k5login

·	·
Operating system	Linux
Difficulty	Hard
Vector	Active Directory
IP	10.10.10.244
Retirement date	2021-06-19
Skills	DNS Enumeration (dnsenum) SQUID Proxy WPAD Enumeration OpenSMTPD v2.0.0 Exploit SSH using Kerberos (gssapi) Abusing .k5login file Abusing krb5.keytab file Active Directory

Writeups

Language	Author	Format	Link
🇪🇸 ES	S4vitar	Vídeo	Open
🇬🇧 EN	0xdf	Texto	Open
🇬🇧 EN	IppSec	Vídeo	Open

Skill resources

Curated documentation for each technique listed in the Skills column above. Sources: HackTricks, GTFOBins, PortSwigger, etc.

Skill	Source	Link
Active Directory	HackTricks	Open

Related skills worth mastering

Kerberoasting · AS-REP Roasting · DCSync · BloodHound · Group Policy Preferences (GPP) · GetNPUsers (Impacket)

If you liked this machine, try

• Querier — Windows, Medium
• Mantis — Windows, Hard
• Object — Windows, Hard
• Reel — Windows, Hard
• Intelligence — Windows, Medium

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Last updated: 2026-06-07