OpenVPN is an open-source software application that creates secure, encrypted connections over the internet, known as a Virtual Private Network (VPN). It allows users to secure their network traffic, access remote networks safely, and mask their real IP addresses by routing traffic through a VPN server. OpenVPN works by using encryption protocols like SSL/TLS to establish a secure tunnel between a user's device and a remote server, typically configured through a provided .ovpn file. Once connected, all data travels through this encrypted tunnel, protecting it from hackers and eavesdroppers. In environments like TryHackMe, OpenVPN is essential for securely connecting a local machine, such as a Kali Linux VM, to a private network of virtual machines, enabling users to interact with and attack targets within a safe and isolated environment.
Download your OpenVPN (OVPN) Configuration File from your TryHackMe account.
OpenVPN (Advanced) ➡️ Download, as shown below.
This will download a .ovpn file (e.g., username.ovpn).
Note: You can reuse this file until it expires (they regenerate every 6 hours or so).
Now that you’ve downloaded your OVPN file, assuming you are in your host machine, it is time to move it to your Kali Linux VM which can be done several ways (e.g., shared folders, drag-and-drop). In this case it’ll be via the drag-and-drop capability.
🔵 Install Guest Additions in Kali Linux VM
Guest Additions is required for drag-and-drop to function. If you haven’t done this yet, run the following commands:
🔹 sudo apt update
🔹 sudo apt install -y build-essential dkms linux-headers-$(uname -r)
🔵 Enable Drag and Drop
While the Kali Linux VM is running, from the top menu, go to: Devices ➡️ Drag and Drop ➡️ Bidirectional (for both directions), or Host to Guest (if you only want to drop files into the VM)
After everything is set:
To avoid drag-and-drop errors, simply drag a file from your host into the Kali Linux VM Desktop window (or vice versa) as shown below. Files are usually dropped into the Desktop or Home folder in Kali Linux VM.
🔵 Make sure OpenVPN is installed in Kali Linux VM
🔹 sudo apt update
🔹 sudo apt install openvpn -y
🔵 Connect to OpenVPN
🔹 sudo openvpn <your_username.ovpn>
Note: Verify you are in the directory where your .ovpn file is located or you are using the full file path (e.g., /home/whitehathero/Desktop/Whitehathero.ovpn) when running the command.
If ran correctly, you should see the “Initialization Sequence Completed” message as shown below, meaning that you’ve successfully connected!
Your Kali Linux VM is now part of the TryHackMe network — you can start pinging and attacking target machines using the IPs listed in a room (usually in the 10.10.x.x range).
🛑 If for any reason you can’t connect using your .ovpn file, re-download your .ovpn file from TryHackMe and start the connection process again.
To avoid connection issues, you’ll need to keep the terminal window running OpenVPN active while you interact with a target machine. If you want to disconnect, press Ctrl + C.
🔵 Verify connection to TryHackMe
🔹 ip a
You should see an interface named tun0 and your assigned OpenVPN IP address, as shown below.
🔹 ping -c 4 10.10.10.10
If you can successfully ping 10.10.10.10 as shown below with 0% packet loss, then you are connected to TryHackMe, also allowing you to ping the provided Target IP Address.
🎉 Congratulations! You’re now successfully connected to the TryHackMe network using OpenVPN. This allows you to participate in challenges and labs directly from your own Kali Linux VM attack machine, using the Target IP addresses provided in each room.
By connecting this way, you're no longer limited by the time constraints of the TryHackMe AttackBox. You gain full flexibility to complete tasks, explore environments, and build your skills at your own pace — all while using your own setup.