I think the stone that fails in this process is posix-spawn . To do this, you can install the pearl locally:
$ gem install rake-compiler -v 0.7.6 $ git clone git://github.com/rtomayko/posix-spawn.git $ cd posix-spawn $ rake gem $ cd pkg/posix-spawn-0.3.6 $ gem install --local posix-spawn-0.3.6.gem
Explanation (from the article I found):
There is an error in the posix-spawn version in gem stores, however this makes it impossible to install using gem on Cygwin
After that, try bundle install again, it should be successful.
Here is the related issue GitHub project
UPDATE I recently installed scoop command-line installer for Windows, a fairly simple setup. I installed Ruby, bundler and octopress without breaking a sweat. You must try.
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