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OpenSSH and RDP issues


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SSH problem:  I've spun up a Windows Server Core 2016 VM for the first time in a while, and was curious as to whether OpenSSH-Win32 (well, the 64bit version that is) could be setup on this platform. I have it working on Windows Server Core 2K12R2 and of course on Windows Server Core 2019. I got the latest 8.1.0-beta, then unzipped it in C:\Program Files\OpenSSH-Win64\, made the C:\ProgramData\ssh dir, run the install-sshd.ps1, started sshd and ssh-agent and ran the FIxHostPermissions.ps1 after adding my sshd_config to C:\ProgramData\ssh. I also opened port 22/tcp of course. WIth Win2K12R2 this yields a working ssh server. On 2016, I can only ssh to localhost, which works, as local Administrator or AD user. Everything else times out, tested from various boxes using the usual syntax of Administrator@WIN2016@win2016.mydomain.lan (syntax which works on 2K12R2 and 2019) and the equivalent for the AD user. I haven't the faintest idea what's wrong here, but maybe it's linked to my OTHER issue...


RDP problem: I can rdp to an unpatched WIn2016 Server Core using Remmina, the gnome frontend tool for various remote protocols. Once I apply the latest updates, I can no longer do that. xfreerdp does work for Administrator but not for AD user. And using Windows 10's Remote Desktop Connection AD user can log in. Also I can't manage this box via WinRM in Windows Administrative Center, despite 5985/tcp being open. I vaguely remember having these problems back in 2016ish with Remina but solved it using xfreerdp, but AD user not being able to is new to me. I've tried switching from All Connections to NTLM Auth and back in sconfig, doesn't seem to make a difference. My not being an expert Windows Admin means I'm not sure how to narrow things down via Get-Event in powershell. It reminds me I should probably get the Windows VMs to log centrally like the *NIX VMs do.


Hopefully one of you has run into these problems before and solved them?

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