Can not ChrootDirectory
I have tried every way I know how. Every time I try to set ChrootDirectory on OpenSSH server Windows 10, it breaks the service. I can not start the service with ChrootDirectory enabled. All other options I need in sshd_config are working, but as soon as ChrootDirectory is uncommented in config, the service stops and cannot be restarted! Where is the workaround? I see articles about this issue all the way back from 2016, but no word of it being fixed. Microsoft Docs says it is now supported, but I am running latest version and can not get it to work
SSHD service wouldn't start if the sshd_config file has incorrect entries. You can run the sshd.exe in the interactive mode (.\sshd.exe -ddd) to see the error message.
I had the same problems, see my comment below maybe it helps: https://github.com/PowerShell/Win32-OpenSSH/issues/1941#issuecomment-1160288014