If you work with Ruby on Windows in a corporate environment, sooner or later, you will hit an error when you are trying to install or update Gems. In my case, I simply had to set a few environment variables and I was good to go. RubyGems uses the HTTP_PROXY, HTTP_PROXY_USER and HTTP_PASS by default so if you open up a command prompt and set these as follows, it will use them to find the proxy and authenticate you to your proxy server:
set HTTP_PROXY=http://pr.oxy.ip:port set HTTP_PROXY_USER=domain\user.name set HTTP_PASS=sUp3rS3curepAs$w0rd
Extra points: A reader sent me a comment that this will only work when the proxy is using basic authentication. If you're having trouble using this method then you can give ntlmaps a shot. It's basically a little bit of python magic that sets up a proxy on your localhost through which you can route traffic and it will handle the authentication with your proxy server for you.