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Windows 10 + Stunnel + OpenVPN
Configuring Windows 10 to use OpenVPN over Stunnel
Requirements
This article assume you already have a working Stunnel and OpenVPN server running somewhere. If you haven’t set up the servers yet, feel free to browse how I managed to set this up on a server. Here are the links where I’ve set up a Ubuntu 16.04 and 18.04 OpenVPN server respectively with the relevant Stunnel setup.
Installing Stunnel on Windows 10
Download stunnel from https://www.stunnel.org/downloads.html. I chose the latest win64 installer.exe and install.
During the installation process, you will be prompted to add create a stunnel.pem file. Just hit enter for everything now because we will be updating the stunnel.pem file with our own stunnel.pem file later.
Finally, open stunnel after installation.
Once everything is installed, you should be able to see the stunnel icon in your system tray. Right click to open the context menu and click on “Edit Configuration”
Now you should be able to see the configuration file in your default text editor. Feel free to remove all the boilerplate configuration and update this to your own. What is important is the port number, which should be the same as your OpenVPN configuration file later. Here we set it to 1338. Finally, ensure that you use either your domain or ip address in “connect” parameter.
