Ruby woes - gems won't work, "could not find valid gem 'sass'" port 443<>
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- Install SASS using gem on Windows 8 3 answers
Generally this is the result of a super strict application firewall setting. Sometimes applications are restricted in the sorts of external connections they can make and this can interfere with the Ruby Gem downloading process.
Make sure your Ruby process has access to port 443 when making external connections.