Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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Windows isn’t typically meant to run manually installed web servers or apps that would also run on Linux.
For example, unless you’re Microsoft you wouldn’t set up IIS just to run a web server and manually configure it all unless you had a good reason.
Microsoft Windows Server absolutely excels at this though - Apps built for Windows. If an app is built for Windows then you typically don’t have to do the manually fiddly stuff like authentication and database setup. It will typically do it for you. It will just be an Exe you run and click next next and you’re done.
So I would recommend one of the following
The best example app I can think of that is made for Windows that would need Windows Server and is so simple to install is PRTG or Veeam B&R. Both huge apps in Enterprise and both only run on Windows.