Before jumping into the tryhackme machines and starting this journey, i want to share my configs — what I did on tryhackme to make a stable setup for solving the challenges.

Note: My TryHackMe account is on the free plan.

I want to share a few basics: how to sing up, setup an OpenVPN connection, and my configs for connection to and interacting with the machines.

TryHackMe setup

1. Create an account on TryHackMe

At the beginning, create a free account on the TryHackMe platform with your email:

• Here: https://tryhackme.com/signup

1.1. Download your OpenVPN configuration

After creating your account, go to the Profile → VM & VPN Settings and click the Download Regular Configuration File button to get your OpenVPN config file.

1.2. Connect using your OpenVPN configuration

After downloading the config, move it to the OS you’ll use to connect to TryHackMe ( e.g., a Linux VM ).

You can use this command on a Linux system ( e.g., Kali ):

sudo openvpn --config eu-west-1-mahyar-regular.ovpn

If you see a log like this ( Initialization Sequence Completed ), and get an IP on tunX, your connection is successful.

2. Launch a Machine

After connection to TryHackMe via OpenVPN, pick a machine, start it, and connect to it using the assigned IP.

There are multiple ways to do this; view a machine from your computer; but I’ll explain my flow chart.

These are the assets I use in this CTF series:

• Windows as my main OS
• A Kali Linux VM for my tools
• Burp suite on the Kali Linux VM as a proxy between Windows and Kali
• A VPS used for ssh tunneling on Kali Linux VM for a connection to OpenVPN

For example, the first machine we’ll cover in the next article is:

• https://tryhackme.com/room/brooklynninenine

On that page you’ll see a “Join Room” message/button — click it to join the room.

This message appears at the beginning of each room. Click “Join Room” to activate the room on your profile.

Click the light-green “Start Machine” button in the Task 1 tab.

After a minute the machine will be assigned an IP address, which you can access from your Linux VM connected via OpenVPN:

To verify the connection, you can ping that IP:

2.1. How to view the machine via browser

Almost all TryHackMe machines include a web application accessible via the assigned IP.

There are multi ways too which you can see the web pages from your computer, but here, as i told you, i want to show and explain my flow.

I use VPS because the TryHackMe platform is blocked in my country. So I use an extra layer ( The VPS and SSH tunnel ) to bypass the filter and access the site and lab web pages.

As described, I use Windows as my main OS for browsing, and capture the requests/responses with Burp Suite on the Kali Linux VM.

Note: I browse on Windows because Kali runs as a VM and is slower.

So I browse in Windows, capture traffic in Burp on Kali, and run some tools on the VPS.

I create an SSH dynamic forwarding tunnel from Kali to the VPS ( used as a SOCKS proxy ):

ssh root@[MY-VPS-IP] -q -D 1080

Then, I open Burp Suite on Kali ( the OS with the SSH tunnel ) and set a Proxy listener on 192.168.1.178:8080 and the SOCKS proxy to 127.0.0.1:1080.

Then, I configure Firefox on Windows to use Burp’s proxy; so I can browse the machine from Windows.

Note: my Windows OS and Kali VM are on the same network.

Finally, with this setup, when I load the machine IP in Windows, two things happen:

1. Bypass TryHackMe filtering in my country using the VPN
2. capture the machine’s requests/responses in Burp

And the flow will be something like this:

1. Requests are forwarded to the Kali VM → Burp listener
2. Burp forward the requests to the VPS via the SSH tunnel
3. the VPS forward them to the TryHackMe platform via the OpenVPN connection
4. TryHackMe will forward the requests to the target machine IP on the VPN network
5. Responses follow the reverse path, so you can inspect them in Burp as well.

3. Summary

In this article we learned how to launch a TryHackMe machine and set up a testbed. I also explained the workflow i use for this CTF series. You can follow this setup exactly or adapt it to your own assets.

In the next article of this TryHackMe — All-in-One series, we’ll go straight to the CTF machines, starting with Brooklyn Nine-Nine.