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This gem requires win32-security on Windows hosts, but that's not properly defined in the gemspec. Since the gemspec is parsed by rubygems and uploaded the logic to include that windows depedencies on windows is only included when the gem is uploaded from a windows host. Instead you want to define a universal-mingw32 gemspec that adds additional dependencies on Windows. Then you push both platforms of gems via the two gemspec and windows hosts automatically pull the correct platform with the additional dependency. An example of doing this is the chef gem which includes two gemspecs:
This gem requires win32-security on Windows hosts, but that's not properly defined in the gemspec. Since the gemspec is parsed by rubygems and uploaded the logic to include that windows depedencies on windows is only included when the gem is uploaded from a windows host. Instead you want to define a universal-mingw32 gemspec that adds additional dependencies on Windows. Then you push both platforms of gems via the two gemspec and windows hosts automatically pull the correct platform with the additional dependency. An example of doing this is the chef gem which includes two gemspecs:
https://github.com/chef/chef/blob/master/chef.gemspec
https://github.com/chef/chef/blob/master/chef-universal-mingw32.gemspec
and produces different gem platforms on rubygems:
https://rubygems.org/gems/chef
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