WSE WorkFolders on Win Server 2019


I know Windows Server Essentials Version can’t be used because it doesn’t support Windows Anywhere / Remote Access.

I was wondering if I could use LAN & OpenVPN access (instead of Anywhere / Remote) on Server 2019 with Essentials Licensing & Essentials Experience.  My pfSense router is already setup for OpenVPN which I use when I’m offsite already.

I’m only asking as I am thinking to roll my Media and Home Automation needs into my next windows Server build, but concerned the device CALs will significantly drive up the license costs.

I was originally considering Windows Server 2016 Essentials, but Mike’s recent glowing reviews of Server 2019 has me thinking that might not be so wise.


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Good Answer

Alas, I’m afraid not. WSE WorkFolders (and the Work Folders server role in general) is designed to work over a secure HTTPS (TCP port 443) connection, and not a VPN connection.

While you certainly can manually configure IIS on Windows Server 2019 Essentials in order to set up your own webserver, WSE WorkFolders makes the assumption that a website has not been set up on the Essentials server unless the Anywhere Access / Remote Web Access feature of WSEE has been properly configured. And since that cannot be done on Windows server 2019 Essentials, WSE WorkFolders cannot be used on it.

However, since Windows Server 2019 Essentials does not actually include “Essentials” (LOL – I can’t believe that I have to actually type that nonsense – stupid Microsoft!), you don’t need to worry about the Work Folders server role conflicting with the WSEE server role. Therefore, if you just leave the “Essentials” bits off of the server, then you can configure the Work Folders server role on Windows Server 2019 Essentials as usual (i.e. just as you would under a stock Windows Server 2019 Standard install).

WSE WorkFolders was developed in order to resolve the issue where the WSEE server role and the Work Folders server role conflict with each other since they are both webservers that fight over the HTTPS port 443 connection. Obviously, since Windows Server 2019 Essentials doesn’t contain the “Essentials” bits, there’d be no conflict, and so you can use the Work Folders server role on it just as the role exists within the Server Manager (after you’ve manually configured your server to be a webserver via IIS that is).

So basically, if the main focus of your Windows Server 2019 Essentials server is to use Work Folders, then you don’t need to install WSEE nor WSE WorkFolders on it. You can just set up the Work Folders server role on it normally. However, if you’re actually wanting the “Essentials” functionality (Remote Web Access, Client PC backups, etc., etc.), then you’ll need to use Windows Server 2019 Standard/Datacenter with WSEE installed, and then use WSE WorkFolders in order to get the Work Folders functionality.

I personally wouldn’t worry about CALs. There’s no pace to enter them (even if you do buy them), and no one is ever going to come knocking on your door looking for them (i.e. they’re a complete waste of money unless you just need them for the “piece of mind” comfort that they’d offer you). The only thing that stinks here is the large price difference between Windows Server 2019 Essentials and Windows Server 2019 Standard.

I hope that makes sense.

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