Hack The Box - HTB Layover Writeup - Medium- Weekly - September 26th, 2026

September 26, 2026

Machine Name: Layover Operating System: Linux Difficulty: Medium Executive Summary Layover is a medium-rated Linux box themed around a corporate airport network. The path to compromise opens with an RDP session against a loosely secured jumpbox, then moves through a simulated virtual WiFi segment where plaintext credentials can be sniffed off the wire. Those credentials unlock a Remote Code Execution (RCE) flaw in Craft CMS, which in turn enables lateral movement over SSH. Root is reached by abusing a local privilege escalation bug in the CUPS printing service. 1. Initial Access & Enumeration …