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

Question

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

I've been using cntlm (http://cntlm.sourceforge.net/) at work. Configuration is very similar to ntlmaps.

• gem install --http-proxy http://localhost:3128 _name_of_gem_

Works great, and also allows me to connect my Ubuntu box to the ISA proxy.

Check out http://cntlm.wiki.sourceforge.net/ for more information

I tried some of these solutions, and none of them worked. I finally found a solution that works for me:

gem install -p http://proxy_ip:proxy_port rails

using the -p parameter to pass the proxy. I'm using Gem version 1.9.1.