I'm not behind a firewall, but I've been hearing several reports from 
people that that they are not able to get the HTTP_PROXY setting for the 
gem install command to work correctly. This worries me because several 
people have been trying to workaround this problem by downloading gems 
locally. I am not in favor of this solution, because it seems 
unmaintainable. I don't know how to keep an up-to-date list of all the 
require gems, since the gems required by the watir gems themselves are 
subject to changes that I don't track.

Therefore I've done some research on the HTTP_PROXY problem. There are 
several reports that this does now work a particular type of Windows 
proxy. Could some one who is facing this problem review this reports and 
let me know whether they represent practical solutions to this problem?

Bret


http://exceptionz.wordpress.com/2008/03/18/run-gem-install-behind-a-firewall-in-windows/

Next we install the Ruby Win32 SSPI 
<http://rubyforge.org/projects/rubysspi/> which gives ruby the ability 
to authenticate with ISA natively. We need this library because as far 
as I understand, it patches the Open-uri library because of some 
incompatibilities with windows.


http://www.rubygems.org/export/html/3


      Authenticating Windows Proxy Problems

/How can I install a gem from behind a Windows proxy that requires 
authentication? I’ve tried *username(colon)password(at)proxyaddress* in 
the—http-proxy url but that doesn’t seem to work./

This suggests you’re behind an MS Proxy that does NTLM authentication. 
The proxy support in Ruby is currently only for Basic authentication.

A workaround is to install http://apserver.sourceforge.net apserver 
<http://apserver.sourceforge.net> 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



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