OpenVPN won't connect on Windows 10 - Solved

Posted on Monday, December 14, 2015 at 1:53 PM into openvpn, windows10, code & gotcha by Steve Woods.
Roughly a 1 minute read.

I work with some colleagues who use OpenVPN to connect to their SVN repository and as such have to authenticate via a VPN tunnel before I can checkout the existing codebase.

However, every single time I update Windows 10 to the latest version (which is mandatory after a while!), the OpenVPN software then fails to connect - with a brilliant and informative error "Failed to connect". Nothing in the logs, nothing in the Event Logs.

After tearing out what little hair I have left, I came across a solution on Reddit of all places - just reinstalling the OpenVPN client won't work, you have to also reinstall the TAP drivers for OpenVPN by downloading https://swupdate.openvpn.org/community/releases/tap-windows-9.21.1.exe .

Once downloaded, you have to run the TAP update script, but you MUST run it as an Administrator, else it'll fail.

• Click the Start Menu icon.
• Go to All Apps
• Scroll down to TAP Windows
• Right click on Add a new TAP Virtual Ethernet Adapter
• Click on "More Options"
• Click on "Run as Administrator"

Now install the OpenVPN client from your VPN address, and it should connect fine once done.