OpenVPN Windows Server: A Comprehensive Guide for Devs

Greetings, Devs! Today, we will discuss everything you need to know about OpenVPN Windows Server. OpenVPN is a virtual private network (VPN) protocol that lets you extend your local network to different locations securely. In this guide, we’ll walk you through the process of setting up OpenVPN on a Windows server, including the essential configurations, troubleshooting tips, and frequently asked questions.

What is OpenVPN?

OpenVPN is a secure VPN protocol that offers high-level encryption to ensure secure data transfer between connected devices. The protocol was created by James Yonan in 2001 and has since become one of the most widely used VPN protocols in the world. OpenVPN uses SSL/TLS encryption to secure the connection between two devices, and it supports both TCP and UDP protocols, making it flexible and versatile.

OpenVPN is an open-source project, which means that anyone can access its source code and modify it to suit their needs. The protocol is free to use, and it’s constantly being updated to address any security issues.

Setting up OpenVPN on a Windows Server

Setting up OpenVPN on a Windows server is a relatively straightforward process that requires some technical expertise. Here are the basic steps:

  1. Choose a Windows server that meets the system requirements for OpenVPN.
  2. Download the latest version of OpenVPN for Windows.
  3. Install OpenVPN on your Windows server.
  4. Configure your OpenVPN server settings.
  5. Generate your SSL/TLS certificates and keys.
  6. Configure your client settings and connect to the VPN.

Step 1: Choosing the Right Windows Server

The first step in setting up OpenVPN on a Windows server is to choose a server that meets the system requirements for OpenVPN. The server should be running Windows Server 2008, Windows Server 2012, or Windows Server 2016. It should have a static IP address and a stable internet connection.

Step 2: Downloading OpenVPN for Windows

Once you’ve chosen your Windows server, the next step is to download the latest version of OpenVPN for Windows from the official website. You can choose between the community version, which is free, and the enterprise version, which is paid for and includes support and additional features.

Step 3: Installing OpenVPN on Your Windows Server

To install OpenVPN on your Windows server, follow these steps:

  1. Extract the OpenVPN installation files to a folder on your Windows server.
  2. Run the OpenVPN installer as an administrator.
  3. Follow the prompts to install OpenVPN.
  4. When the installation is complete, you should see the OpenVPN GUI client in your system tray.

Step 4: Configuring Your OpenVPN Server Settings

The next step is to configure your OpenVPN server settings. This involves creating a configuration file that specifies your server’s IP address, port number, and other settings. Here’s an example configuration file:

push “dhcp-option DNS”
push “dhcp-option DNS”

Once you’ve created your configuration file, save it to the OpenVPN config directory, which is typically located at C:\Program Files\OpenVPN\config.

Step 5: Generating Your SSL/TLS Certificates and Keys

SSL/TLS certificates and keys are essential for securing your OpenVPN connection. To generate your certificates and keys, follow these steps:

  1. Open a command prompt as an administrator.
  2. Navigate to the C:\Program Files\OpenVPN\easy-rsa directory.
  3. Run the init-config.bat file to create a configuration file.
  4. Run the vars.bat file to set your environment variables.
  5. Run the init-ca.bat file to create your certificate authority (CA) certificate.
  6. Run the build-key-server.bat file to create your server certificate and key.
  7. Run the build-dh.bat file to create your Diffie-Hellman (DH) parameters.
  8. Copy the CA certificate, server certificate, server key, and DH parameters to the OpenVPN config directory.
READ ALSO  SQL Server Window Functions: A Comprehensive Guide for Dev

Step 6: Configuring Your Client Settings and Connecting to the VPN

Finally, you need to configure your client settings and connect to the VPN. Here’s how:

  1. Download the OpenVPN client software from the official website.
  2. Install the OpenVPN client on your local machine.
  3. Copy the client certificate and key from the OpenVPN config directory to your local machine.
  4. Open the OpenVPN client and import the client certificate and key.
  5. Enter the IP address and port number of your OpenVPN server.
  6. Connect to the VPN.

Troubleshooting Common OpenVPN Windows Server Issues

Setting up OpenVPN on a Windows server can be challenging, and it’s not uncommon to run into issues along the way. Here are some common issues you might encounter and how to fix them:

Issue 1: OpenVPN Cannot Connect to the Server

If OpenVPN cannot connect to your server, there are several possible causes. First, check that your server’s firewall is properly configured to allow OpenVPN traffic on the correct port. Also, check that your server’s IP address and port number are correct in your client configuration file. If these settings are correct, try restarting both the OpenVPN server and client.

Issue 2: SSL/TLS Handshake Failed

If you encounter an SSL/TLS handshake failed error, it means that the client and server cannot establish a secure connection. This issue can be caused by a variety of factors, including incorrect SSL/TLS certificates, incorrect encryption settings, or a mismatch between the client and server’s encryption protocols. To resolve this issue, double-check your SSL/TLS certificates and encryption settings, and make sure that both the client and server are using the same encryption protocol.

Issue 3: OpenVPN Connectivity Issues on Windows 10

Windows 10 has been known to have connectivity issues with OpenVPN. One of the most common issues is the TAP driver not being installed correctly. To fix this issue, try reinstalling the TAP driver or running OpenVPN with administrator privileges.

Frequently Asked Questions

1. Is OpenVPN free?

Yes, OpenVPN is an open-source project and is free to use. However, enterprise versions of the software are available for purchase and offer additional features and support.

2. Can OpenVPN be used on Windows?

Yes, OpenVPN can be used on Windows. The software is available for download on the official website.

3. How secure is OpenVPN?

OpenVPN is considered to be one of the most secure VPN protocols available. The software uses SSL/TLS encryption, which offers a high level of security and is difficult to crack.

4. Do I need technical expertise to set up OpenVPN on a Windows server?

Yes, setting up OpenVPN on a Windows server requires some technical expertise. However, there are many resources available online to help you through the process.

5. What are some common issues with OpenVPN on Windows?

Common issues with OpenVPN on Windows include connectivity issues, SSL/TLS handshake failures, and TAP driver installation issues.


Setting up OpenVPN on a Windows server can be challenging, but it’s an essential step in ensuring the security of your network. By following the steps outlined in this guide and troubleshooting any issues you encounter, you can create a secure and reliable VPN connection for your organization.