I have next to no Windows experience but a lot of Linux experience. An upcoming engagement will require me to install and run our startup's Rails/MySQL software on a Windows 2008 server. Where do I start learning basic things like how to log in via ssh, how to check out a git repository, how to set up MySQL, etc. though a ssh connection? I don't plan on using VNC, just whatever is the Windows equivalent of a bash session over ssh.
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You are, to some extent, looking at this wrong. The functional equivalent of SSH on windows is remote desktop which is a gui environemnt, or really a remote desktop. It is a different world, you can't expect it to behave like *nix. That said, if you want command line level access I'd recommend powershell which blows bash away in many respects.
All that said, you should check out:
All that said, why are you trying to launch this on windows?