Chiming in a bit late, hoping it will be useful though!

 > Yeah, but who wants to **deploy** Ruby code on Windows?

I do deploy Ruby code on Windows (production), just not for public facing
web apps.

For instance, I have MRI 1.8.6 data crunching (datawarehouse) running on
Windows.

I also run JRuby on Windows (see
http://blog.logeek.fr/2010/8/2/on-jruby-resque-and-windows) to interact with
APIs that run only on Windows and to generate PDFs (the web front-end is
itself running on Ubuntu).

I have another client who has been able to automate an amazing amount of
work in their company, thanks to relying on Ruby, OLE or other APIs (they
work with many tools such as SAS, Excel, Access).

I am for one *very* happy by the work put by both the JRuby team and the
RubyInstaller project to ensure things work properly there (and obviously,
by the IronRuby team too :-).

Just to add a few data points!

-- Thibaut
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