Quick answer: To connect Windows to TryHackMe, download your .ovpn file from the TryHackMe Access page and install OpenVPN GUI from openvpn.net. Then right-click the OpenVPN tray icon, choose Import file…, pick your .ovpn, and click Connect. When the icon turns green, run ipconfig. An adapter with a 10.x.x.x address means you’re connected.

TryHackMe OpenVPN Windows Room Walkthrough Users

Welcome to this step-by-step TryHackMe OpenVPN setup guide for Windows! This walkthrough will help you securely connect your Windows system to the TryHackMe network using OpenVPN GUI, enabling you to participate in labs that require a private connection.

What Is the TryHackMe OpenVPN Room?

“A guide to connecting to our network using OpenVPN.”

TryHackMe’s OpenVPN room helps users configure their systems to access private machines that cannot be accessed through the browser. This guide is designed specifically for Windows users.

Access the Lab: TryHackMe OpenVPN Windows

YouTube Video Walkthrough for Windows Users

Prefer video instructions? Watch the full OpenVPN setup for Windows here:

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Step 1: Download Your OpenVPN Configuration File

1. Go to the Access Page on TryHackMe.
2. Click on “Download My Configuration File”.

Downloading .ovpn File
Save the .ovpn file to a known folder, e.g., C:\Users\YourName\Downloads\TryHackMe.

Step 2: Install OpenVPN GUI for Windows

1. Visit the official OpenVPN Community Downloads page.
2. Download the OpenVPN installer for Windows.
3. Run the installer and complete the setup with default options.

After installation, you’ll see an “OpenVPN GUI” shortcut on your Desktop.

Step 3: Import your configuration file

1. Find the OpenVPN GUI icon in the system tray (bottom-right; click ^ if it’s hidden).
2. Right-click it and choose Import file…
3. Select your .ovpn file. You’ll see “File imported successfully.”

Older method: copy the .ovpn file into C:\Users\<YourName>\OpenVPN\config\ (or C:\Program Files\OpenVPN\config\), then restart OpenVPN GUI.

Step 4: Connect to the TryHackMe VPN

Right-click the tray icon and click Connect. When the icon turns green and the log shows Initialization Sequence Completed, you’re on the TryHackMe network. On older versions, run OpenVPN GUI as administrator if Connect fails.

Step 5: Confirm VPN Connection

Open Command Prompt and run ipconfig. Look for an adapter called OpenVPN Data Channel Offload, Wintun or TAP-Windows Adapter V9 with an address starting 10.. You can also refresh the TryHackMe Access page: it should say Connected and show your internal IP.

If this adapter shows an IP starting with 10.x.x.x, you’re successfully connected.

Step 6: Deploy a Machine on TryHackMe

1. Go to any room that requires a VPN.
2. Click Start Machine.
3. You’ll be assigned a TryHackMe internal IP.

You can now interact with the machine using tools like:

• ping <IP>
• Browsing: Open your browser and visit http://<internal-ip>

Troubleshooting OpenVPN on Windows

• “Connecting…” forever / TLS handshake failed: your network may block UDP. Download a TCP config from the Access page, or try another network.
• Connected, but you can’t reach the machine: make sure only one VPN is running. Disconnect any other VPNs (NordVPN, Proton and so on), then reconnect.
• “Multiple sessions” or you keep getting disconnected: you’re connected from another device or tab. Disconnect everywhere else, then download a fresh config.
• No TAP/Wintun adapter: reinstall OpenVPN and accept the driver prompt during setup.
• Still stuck? Use TryHackMe’s in-browser AttackBox instead; it needs no VPN at all.

Conclusion

You’re now connected to TryHackMe from Windows with OpenVPN GUI: import your .ovpn, connect, and check for a 10.x address. If anything fails, check the troubleshooting list or switch to the AttackBox. Using Linux instead? See the TryHackMe OpenVPN on Linux guide. Then follow my TryHackMe Roadmap for the next rooms.

Frequently Asked Questions