How do I update Ruby Gems from behind a Proxy (ISA-NTLM)

For the Windows OS, I used Fiddler to work around the issue.

1. Install/Run Fiddler from www.fiddler2.com

2. Run gem:

   $ gem install --http-proxy http://localhost:8888 $gem_name
   

I wasn't able to get mine working from the command-line switch but I have been able to do it just by setting my HTTP_PROXY environment variable. (Note that case seems to be important). I have a batch file that has a line like this in it:

SET HTTP_PROXY=http://%USER%:%PASSWORD%@%SERVER%:%PORT%

I set the four referenced variables before I get to this line obviously. As an example if my username is "wolfbyte", my password is "secret" and my proxy is called "pigsy" and operates on port 8080:

SET HTTP_PROXY=http://wolfbyte:secret@pigsy:8080

You might want to be careful how you manage that because it stores your password in plain text in the machine's session but I don't think it should be too much of an issue.

This totally worked:

gem install --http-proxy http://COMPANY.PROXY.ADDRESS $gem_name