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.

Latest versions of stunnel on the official stunnel website

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.

Installation popup for stunnel.pem file generation

Finally, open stunnel after installation.