TryHackMe – OpenVPN Room Walkthrough for Windows 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.

Room Description

“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

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.

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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.

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Step 3: Add Your Configuration File

1. Copy your downloaded .ovpn file.
2. Paste it into this directory: arduinoCopyEditC:\Program Files\OpenVPN\config\
3. When prompted by Windows for admin permissions, click Continue.

OpenVPN GUI can only read config files in the config folder.

Step 4: Connect to TryHackMe VPN

1. Right-click the OpenVPN GUI on your desktop and select Run as Administrator.
2. Find the OpenVPN icon in the system tray (bottom-right corner of the screen).
3. Right-click it, then click Connect.

OpenVPN GUI Connect Menu
Wait for the connection to establish. You’ll see a message:

Initialization Sequence Completed

Step 5: Confirm VPN Connection

Once connected, your machine will have a virtual interface with the TryHackMe internal IP.

To verify:

1. Press Windows + R, type cmd, and press Enter.
2. Type: nginxCopyEditipconfig
3. Look for an adapter labeled “TAP-Windows Adapter V9” or similar.

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>

Conclusion

Congratulations, you’re now securely connected to the TryHackMe network from your Windows machine using OpenVPN. You’re all set to dive into vulnerable machines, hacking scenarios, and real-world simulations!