Once upon a late-night session in the cyber underground, I stumbled across a fresh “Expressway” box on HackTheBox — a promised route to digital mastery and a cautionary tale of misconfigured VPN gateways and homemade privilege escalation tools. Like a true cyber-detective, I geared up, eager for something deeper than just artifact hunting. This wasn’t just about flags — it was about learning.

Chapter 1: Recon — Listening for Opportunity

The Opening Scene

Imagine the network as a vast, silent street—shrouded in shadows. My first step: turn on the headlights and see what’s out there.

TCP Scan — First Pass, False Comfort

nmap -p- -T4 -sS 10.10.11.87 -oN initial_tcp_scan.txt

SSH (port 22) greets me and then slams the door in my face. No welcome mat here. The box seems as silent as a ghost. Seasoned hackers know—if you only look for doors, you might miss the windows.

The UDP Angle — Where All the Clues Hide

sudo nmap -sU 10.10.11.87 --min-rate 5000

Port 500 lights up. IPsec/IKE. VPN land: hostile territory for most, but a playground for those who know the rules.

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