[zeugma]

Windows Nano Server is headless and sessionless. As mentioned, there is no GUI. But there’s also no local login, so there’s no point in attaching a keyboard or mouse or running this in any kind of Remote Desktop-oriented session. Consider it like a Linux box in the cloud that you don’t have SSH access to – you use it remotely, you manage it remotely, and all it does is run services and applications like an appliance would. It’s incredibly compact and has a very small surface area – just as much as is needed to fulfill its role as a specialty purpose server operating system.

OK, so how do you administer it? How do you authenticate for this administration? Are connections to it encrypted? How do you get files to it to install software and services?

[tacticalogic]

OK, so how do you administer it? How do you authenticate for this administration? Are connections to it encrypted? How do you get files to it to install software and services?

You can either use GUI-based tools installed on your local workstation, or remote Powershell sessions running on the server. These sessions are over HTTPS, so they are encrypted. You can use normal Windows domain authentication, but you can only do a network logon. Local/interactive logons are not allowed (no local console).

You can move files to it over SMB, and they've added the capability to do a file copy tunneled in the same HTTPS connection you're using for the remote Powershell session.