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HowTo: Get passwordless SSH working on Cygwin

I’m sure many out there is actively using Cygwin because they can’t stand being on a Windows platform.  I for one am one of those people.  I install Cygwin on any Windows based servers to login to it remotely via SSH and do what I need to do.

Recently I came across an issue where I had to login from server to server within Cygwin environment via passwordless SSH.  I had already installed openssh server and it was running as a service.  HOWEVER!  It was installed under the default “SYSTEM” windows user and as a result I could never get it working.

Finally, I came across some sources that pretty much indicated that in order for passwordless SSH to work in Cygwin, SSH server must be installed under it’s own user such as sshd_server.

Once I did that, it all worked out!

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