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Actually the best way I found to solve this in windows for Ruby itself, not just one gem, is to do the following:
Download http://curl.haxx.se/ca/cacert.pem into c:\railsinstaller\cacert.pem
Go to your Computer -> Advanced Settings -> Environment Variables
Create a new System Variable:
Variable: SSL_CERT_FILE
Value: C:\RailsInstaller\cacert.pem
Close all your command prompts, including your Rails server command prompt, etc. Start a new ruby irb prompt, and try the following: