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

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

Quick answer : Add proxy configuration with parameter for both install/update

gem install --http-proxy http://host:port/ package_name

gem update --http-proxy http://host:port/ package_name

Posts abound regarding this topic, and to help others save hours of trying different solutions, here is the final result of my hours of tinkering.

The three solutions around the internet at the moment are: rubysspi apserver cntlm

rubysspi only works from a Windows machine, AFAIK, as it relies on the Win32Api library. So if you are on a Windows box trying to run through a proxy, this is the solution for you. If you are on a Linux distro, you're out of luck.

apserver seems to be a dead project. The link listed in the posts I've seen lead to 404 page on sourceforge. I search for "apserver" on sourceforge returns nothing.

The sourceforge link for cntlm that I've seen redirects to http://cntlm.awk.cz/, but that times out. A search on sourceforge turns up this link, which does work: http://sourceforge.net/projects/cntlm/

After downloading and configuring cntlm I have managed to install a gem through the proxy, so this seems to be the best solution for Linux distros.

A workaround is to install http://web.archive.org/web/20060913093359/http://apserver.sourceforge.net:80/ on your local machine, configure it and run gems through this proxy.

• Install: Just download apserver 097 (and not the experimental 098!) and unpack.
• Configure: Edit the server.cfg file and put the values for your MS proxy in PARENT_PROXY and PARENT_PROXY_PORT. Enter the values for DOMAIN and USER. Leave PASSWORD blank (nothing after the colon) – you will be prompted when launching it.
• Run apserver: cd aps097; python main.py
• Run Gems: gem install—http-proxy http://localhost:5865/ library

for anyone tunnelling with SSH; you can create a version of the gem command that uses SOCKS proxy:

1. Install socksify with gem install socksify (you'll need to be able to do this step without proxy, at least)

2. Copy your existing gem exe

   cp $(command which gem) /usr/local/bin/proxy_gem
   

3. Open it in your favourite editor and add this at the top (after the shebang)

   require 'socksify'
   
   if ENV['SOCKS_PROXY']
     require 'socksify'
     host, port = ENV['SOCKS_PROXY'].split(':')
     TCPSocket.socks_server = host || 'localhost'
     TCPSocket.socks_port = port.to_i || 1080
   end
   

4. Set up your tunnel

   ssh -D 8123 -f -C -q -N user@proxy
   

5. Run your gem command with proxy_gem

   SOCKS_PROXY=localhost:8123 proxy_gem push mygem