Hack The Box - HTB Checkpoint Writeup - Medium - Weekly - June 13th, 2026

June 13, 2026

HTB: Checkpoint — Detailed Writeup (redacted, command-by-command) Target: (DC01) · Attacker: (tun0) 0. Environment setup — two gotchas that will waste hours if missed Before any of the attack works reliably, two environmental issues must be fixed. These are not part of the "intended" path but are real over the HTB VPN against a Server 2025 DC. 0.1 The VPN path‑MTU black hole Symptom: small requests (auth, LDAP queries, getting a TGT) succeed, but anything that produces a large request silently hangs forever — specifically the dMSA Kerberos TGS‑REQ (~1.6 …