Remote SSH plugin states VS Code Insiders has experimental support for Windows 10/Server 1803+ using the official OpenSSH server.
I have the official OpenSSH server installed and configured on Windows Server 2019 1809. I can connect via pubkey authentication and have PowerShell Core over ssh working as well. I tried both Remote SSH and Remote SSH nightly plugin. At first it was complaining that it couldn't find bash. So I installed git bash and added it to the system path. I get the following error when attempting to connect to my windows server:
[16:02:41.398] Log Level: 3
[16:02:41.399] remote-ssh-nightly@2019.12.24000
[16:02:41.399] darwin x64
[16:02:41.401] SSH Resolver called for "ssh-remote+myserver", attempt 1
[16:02:41.401] SSH Resolver called for host: myserver
[16:02:41.401] Setting up SSH remote "myserver"
[16:02:41.413] Using commit id "e74405d11443c5361c31e2bc341866d146eee206" and quality "insider" for server
[16:02:41.414] Testing ssh with ssh -V
[16:02:41.425] ssh exited with code: 0
[16:02:41.425] Got stderr from ssh: OpenSSH_7.9p1, LibreSSL 2.7.3
[16:02:41.430] Running script with connection command: ssh -T -D 51951 -o ConnectTimeout=15 myserver bash
[16:02:41.430] Install and start server if needed
[16:02:43.451] > 5122b1a5b835: running
> Unsupported architecture: MINGW64_NT-10.0-17763 x86_64
> 5122b1a5b835##27##
[16:02:43.452] Got some output, clearing connection timeout
[16:02:43.710] "install" terminal command done
[16:02:43.710] Install terminal quit with output: 5122b1a5b835##27##
[16:02:43.710] Received install output: 5122b1a5b835##27##
[16:02:43.710] Unsupported architecture
[16:02:43.711] Resolver error: The remote host's architecture is not supported
[16:02:43.714] ------
Anybody know the magic sauce to get Remote SSH working w/ Windows 10/Server?
Looks like VSCode is attempting to run bash on the server which I'm guessing would resolve to git's bash which is mingw based as I recall. VSCode should be running Powershell on the server.
Did you include your server in the list of windows remotes in the extension's settings?