Otdfbt

I'm trying to set up an SSH server on my Windows2k8 server. I used the instructions found here. Here's the verbose output:

steves-air:~ steve$ ssh steve@mydomain.ca -v
OpenSSH_7.9p1, LibreSSL 2.7.3
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 48: Applying options for *
debug1: Connecting to mydomain.ca port 22.
debug1: Connection established.
debug1: identity file /Users/steve/.ssh/id_rsa type -1
debug1: identity file /Users/steve/.ssh/id_rsa-cert type -1
debug1: identity file /Users/steve/.ssh/id_dsa type -1
debug1: identity file /Users/steve/.ssh/id_dsa-cert type -1
debug1: identity file /Users/steve/.ssh/id_ecdsa type -1
debug1: identity file /Users/steve/.ssh/id_ecdsa-cert type -1
debug1: identity file /Users/steve/.ssh/id_ed25519 type -1
debug1: identity file /Users/steve/.ssh/id_ed25519-cert type -1
debug1: identity file /Users/steve/.ssh/id_xmss type -1
debug1: identity file /Users/steve/.ssh/id_xmss-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_7.9
ssh_exchange_identification: read: Connection reset by peer

So far I'm able to get a network connection, indicating that it's not a firewall problem. As a test, I also tried running sshd under cygwin. I was able to get a terminal prompt with that. I'd prefer to use OpenSSH though, since I want to get it working with powershell.

I tried setting the logging level to DEBUG, but i'm not getting any other troubleshooting info from there.

I'd appreciate any guidance.

*edit: Just realized i should mention. I tried putting a hosts.allow file in the %programdata%/ssh directory. That didn't help and I'm not sure if its applicable in this case.

*edit2: I tried running sshd in interactive mode per the troubleshooting steps from here. Windows came up with an appcrash when i tried to connect. Here's the output before it crashed:

PS C:Program FilesOpenSSH> .sshd.exe -d
debug1: sshd version OpenSSH_for_Windows_7.9, LibreSSL 2.6.5
debug1: private host key #0: ssh-rsa SHA256:XXX
debug1: private host key #1: ecdsa-sha2-nistp256 SHA256:XXX
debug1: private host key #2: ssh-ed25519 SHA256:XXX
debug1: rexec_argv[0]='C:\Program Files\OpenSSH\sshd.exe'
debug1: rexec_argv[1]='-d'
debug1: Bind to port 22 on ::.
Server listening on :: port 22.
debug1: Bind to port 22 on 0.0.0.0.
Server listening on 0.0.0.0 port 22.
debug1: Server will not fork when running in debugging mode.
Connection from 192.168.1.39 port 51410 on 192.168.1.3 port 22
debug1: Client protocol version 2.0; client software version 
OpenSSH_7.9
debug1: match: OpenSSH_7.9 pat OpenSSH* compat 0x04000000
debug1: Local version string SSH-2.0-OpenSSH_for_Windows_7.9
debug1: monitor_read_log: child log fd closed
debug1: do_cleanup
debug1: Killing privsep child 10684

It looks like the answer is "you can't get there from here." I found a closed issue on the git which says that w2k8 standard is not supported. I tried installing on a different server that has 2k8R2 on it and that worked easily.

FWIW, you could try Cygwin's port of OpenSSH. If you want to just check and see if it works, you can try this one:

https://github.com/Bill-Stewart/Cygwin-OpenSSH

It does require Windows PowerShell v2 on Vista/Server 2008, though, so you would need to install that first (which you should hopefully have already).