How can I setup "Always ON VPN" to a Windows Server Machine?

We are moving our BDR server offsite. We need it to connect to our local network to continue to take backups of our current server on site. I What I need is for this server to be ‘Always ON’ the VPN when it boots up/loses connection and then reconnects. I can find plenty of guides for windows 10 machines, but I cannot find how to do it on a windows server machine. Any help is appreciated.

Personally, I would configure a site-to-site VPN using two hardware devices such as Sonicwall, or Fortigate, one in each location. Configure the tunnel and boom, now 192.168.3.x always sees 192.168.4.x networks entirely. Plus it’s more secure. I would never ever ever open RDP to the internet, nor would I personally use any Windows software VPN…

I agree with this approach, there is no need to worry if the VPN service is up or anything on your server. Also with a hardware device you can setup a secondary internet connection for your always on requirement.

This makes perfect sense. Thank you.

This is correct technically and compliance wise. The alternative of an active RDP tunnel would be a nightmare if OP’s company is ever audited or has compliance requirements.

Agreed, this is what I would do in a situation where I need two sites always connected.

However, this isn’t one of those situations. You don’t want your BDR permanently connected to your production LAN. Unless you put protections in place, if you get hit with crypto, it’s just going to go cross site and encrypt that too.

nor would I personally use any Windows software VPN…

Why?