HackTheBox – Expressway Walkthrough | IPsec IKE VPN Pentesting, Chwoot

In this HackTheBox machine, we perform comprehensive port scanning including UDP enumeration to discover an IPsec IKE VPN service running on UDP port 500, use ike-scan to test for aggressive mode vulnerabilities and extract pre-shared keys (PSK), crack the PSK hash using hashcat and psk-crack to obtain VPN credentials, SSH into the target with discovered credentials, enumerate with LinEnum-ng, and finally exploit CVE-2025-32463 (chroot/chwoot) for sudo privilege escalation to root. This machine covers VPN pentesting, UDP service exploitation, and modern privilege escalation techniques. If you're learning network pentesting, VPN exploitation, OSCP, or just love seeing machines get popped... this one's for you. 📂 Scripts and Commands: https://strikoder.com/writeups/expres... https://github.com/strikoder/LinEnum-ng 🏠 Room Link: https://www.hackthebox.com/machines/e... -------- ⏱️ Timestamps: 00:00 - Intro & Target Overview 01:03 - TCP Port Scanning with Nmap 01:21 - UDP Port Enumeration Strategy 03:03 - Discovering IPsec IKE on UDP 500 06:03 - Testing for Aggressive Mode 09:19 - Extracting Pre-Shared Key with ike-scan 10:02 - psk-crack Method 10:55 - Cracking PSK with Hashcat 14:40 - Running LinEnum-ng 17:02 - CVE-2025-32463 (Privilege Escalation to Root) -------- Follow me for more real-world hacking walkthroughs, live streams, and cert prep content 👇 💻 Labs GitHub: https://github.com/strikoder 🎥 Streams & Short Content Twitch:   / strikoder   Instagram:   / strikoder   TikTok:   / strikoder   💬 Community & Discussions Discord Server:   / discord   X (Twitter): https://x.com/Strikoder 📨 Official Contact LinkedIn:   / strikoder   Email: [email protected] More videos coming soon on PNPT, and OSCP prep. Stay tuned, and thanks for the support! #expressway #ipsec #ike #vpn #udpenumeration #psk #cve2025 #chroot #ikescan #oscp #pt1 #hackthebox #tryhackme #portswigger #portswiggeracademy #activedirectory #linux #windows #ethicalhacking #cybersecurity #pentesting #ctf #infosec #enumeration #privilegeescalation #windowshacking #networksecurity #bugbounty #RedTeam #capturetheflag #hackingtools #cyberseclabs #hackermindset #Nmap #terminal #strikoder