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Using Cygwin environment on Windows is a very common solution for automation.

I am looking for a script that would automate the cygwin installation and enablement of ssh server.

I could try to write one but one of the problems is that I don't know what I can use to download line for downloading cygwin.

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ftp -s:filename is your friend. –  Iain Jul 2 '13 at 9:23

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Automating the Cygwin installation is described here. Once you've installed Cygwin, you need to run ssh-host-config to set up the ssh server. I don't know how easy that is to automate, but maybe you could do something with expect, and chain the two scripts together.

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