Windows VPN in Windows Std '19 w/ Essentials Services added?


I’m running Windows Standard Server 2019 and added the Essentials role with WSEE Installer. The connector installed a VPN on the clients but it has never worked. I’d really like to get that working and am exploring the docs at Virtual Private Networking (VPN) | Microsoft Docs.

Those docs refer to adding roles. Does doing so have any adverse effect on the current setup? Windows RemoteApp 2016 works well from outside the network with RADC and I really don’t want to break that, especially since I’m 100s of miles and won’t have immediate access to fix something.

Is there something I can reconfigure to get this working? I have access to the server through RemoteApp and to the router by running a browser as a remote app. The router supports OpenVPN and dynamic DNS. The latter is working; the former is not, but I only just started setting it up. I’d much rather use the Windows native client connecting to my server, though.


Edit: my current Windows client is Windows 11 but Windows 10 also failed, from both within and without the network.

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Best Answer

The VPN feature of Essentials belongs entirely to Microsoft, and has nothing to do with the WSEE Installer I’m afraid (i.e. it’s their feature/code and has nothing to do with me nor the WSEE Installer). AFAIK, the VPN feature works as designed (by Microsoft) when the WSEE server role has been installed under Windows Server 2019/2022/vNext (via the WSEE Installer).

I personally, don’t use the VPN feature of Essentials because it does not work when your client computers have been connected to the Essentials server via the SkipDomainJoin method (i.e. it requires that your clients be domain joined to the server in order to function), but AFAIK, it does indeed work.

The only caveat to this is when running under Windows Server 2019… Apparently, under Windows Server 2019 (only), Microsoft seems to have introduced some bugs that prevent VPN from working properly under that platform. For info on how to correct those issues see here.

I hope that helps you out some.

Understanding VPN configuration in Windows Server 2012 R2 Essentials
Troubleshooting Common VPN issues on Windows Server 2012 R2 Essentials
Windows Server 2012 Essentials VPN without port 1723? (and Remote Domain Join)

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I didn’t think it had anything to do with WSEE Installer, but I didn’t want to break anything in WSEE by installing roles suggested in the Microsoft docs.

I use SkipDomainJoin, as well, but may test joining a laptop to see if I can get the VPN to work. If I can, I think enabling the VPN may outweigh the disadvantages of joining a domain if, indeed, there are any that matter to me.

This is just for personal use but we travel a lot with extended times away from home, often on public WiFi. Having a secure VPN that I own and control is not a bad thing.

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