There is an interesting discussion over at Ruby Inside regarding "Is Windows a First Class Platform for Ruby"? I think there are two parts to this question.
Windows is definitely viable as a development platform using Ruby. I build and deployed a Rails website using Windows as the development platform. I had a few problems which I was able to overcome by googling around for a patch or two. No show stopper for sure. All the gems I need were working fine on Windows. A big thanks to those maintainers that kept their gems multi-platforms.
Windows as a deployment platform. I think this is where I draw the line. I didn't even think for a second about deploying the site on Windows. It is definitely not an option at all. Although, I am looking forward to IronRuby and its support for Rails. I know one of their goal is to be able to run Rails. IIS 7 is looking quite nice.
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