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

Asked 2008-08-07T05:21:16.807
242

The firewall I'm behind is running Microsoft ISA server in NTLM-only mode. Hash anyone have success getting their Ruby gems to install/update via Ruby SSPI gem or other method?

... or am I just being lazy?

Note: rubysspi-1.2.4 does not work.

This also works for "igem", part of the IronRuby project

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2 Answers

39

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.

answered 2012-08-01T23:32:44.667
8

I tried all the above solutions, however none of them worked. If you're on linux/macOS i highly suggest using tsocks over an ssh tunnel. What you need in order to get this setup working is a machine where you can log in via ssh, and in addition to that a programm called tsocks installed.

The idea here is to create a dynamic tunnel via SSH (a socks5 proxy). We then configure tsocks to use this tunnel and to start our applications, in this case:

tsocks gem install ...

or to account for rails 3.0:

tsocks bundle install

A more detailed guide can be found under:

http://blog.byscripts.info/2011/04/bypass-a-proxy-with-ssh-tunnel-and-tsocks-under-ubuntu/

Despite being written for Ubuntu the procedure should be applicable for all Unix based machines. An alternative to tsocks for Windows is FreeCap (http://www.freecap.ru/eng/). A viable SSH client on windows is called putty.

answered 2011-09-06T05:04:51.830

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