Latest versions of Ruby and RubyGems were downloaded and installed without incident. Where I ran into a big problem was installing Rails and its dependencies. Initially I tried to run "gem install rails" but the operation failed due to proxy authentication issues, and this is a well known limitation.
I thought that I would manually download and install the gems but this would have taken hours. As usual, a StackOverflow post provided the inspiration to use CNTLM.
Initially I couldn't get CNTLM to authenticate properly because I didn't know the correct authentication type. The CNTLM manual indicated that there is a switch ("-M") that will test various authentication types using "magic NTLM dialect detection" (!). Using "cntlm -M http://www.google.com" revealed the correct mode that I should use. After making the change in cntlm.ini and restarting the CNTLM service I was able to successfully install rails using the following command:
gem install rails --http-proxy http://localhost:3128
Here's a sampling of the errors that I experienced as well as a successful download:
C:\Ruby192\bin>gem install rails --http-proxy http://localhost:3128 C:\Ruby192\bin>gem install rails ERROR: While executing gem ... (Gem::RemoteFetcher::FetchError) too many connection resets (http://rubygems.org/gems/abstract-1.0.0.gem) C:\Ruby192\bin>gem install rails --http-proxy http://localhost:3128 ERROR: While executing gem ... (Gem::RemoteFetcher::FetchError) bad response Not Found 404 (http://rubygems.org/gems/abstract-1.0.0.gem) C:\Ruby192\bin>gem install rails --http-proxy http://localhost:3128 ERROR: While executing gem ... (Gem::RemoteFetcher::FetchError) bad response Proxy Authorization Required 407 (http://rubygems.org/gems/abstract-1.0.0.gem) C:\Ruby192\bin>gem install rails --http-proxy http://localhost:3128 Fetching: abstract-1.0.0.gem (100%) WARNING: abstract-1.0.0 has an invalid nil value for @cert_chain Fetching: erubis-2.6.6.gem (100%) Fetching: actionpack-3.0.7.gem (100%) Fetching: arel-2.0.10.gem (100%) Fetching: activerecord-3.0.7.gem (100%) Fetching: activeresource-3.0.7.gem (100%) Fetching: mime-types-1.16.gem (100%) Fetching: polyglot-0.3.1.gem (100%) Fetching: treetop-1.4.9.gem (100%) Fetching: mail-2.2.19.gem (100%) Fetching: actionmailer-3.0.7.gem (100%) Fetching: thor-0.14.6.gem (100%) Fetching: railties-3.0.7.gem (100%) Fetching: rails-3.0.7.gem (100%) Successfully installed abstract-1.0.0 Successfully installed erubis-2.6.6 Successfully installed actionpack-3.0.7 Successfully installed arel-2.0.10 Successfully installed activerecord-3.0.7 Successfully installed activeresource-3.0.7 Successfully installed mime-types-1.16 Successfully installed polyglot-0.3.1 Successfully installed treetop-1.4.9 Successfully installed mail-2.2.19 Successfully installed actionmailer-3.0.7 Successfully installed thor-0.14.6 Successfully installed railties-3.0.7 Successfully installed rails-3.0.7 14 gems installed Installing ri documentation for abstract-1.0.0... Installing ri documentation for erubis-2.6.6... Installing ri documentation for actionpack-3.0.7... Installing ri documentation for arel-2.0.10... Installing ri documentation for activerecord-3.0.7... Installing ri documentation for activeresource-3.0.7... Installing ri documentation for mime-types-1.16... Installing ri documentation for polyglot-0.3.1... Installing ri documentation for treetop-1.4.9... Installing ri documentation for mail-2.2.19... Installing ri documentation for actionmailer-3.0.7... Installing ri documentation for thor-0.14.6... Installing ri documentation for railties-3.0.7... Installing ri documentation for rails-3.0.7... Installing RDoc documentation for abstract-1.0.0... Installing RDoc documentation for erubis-2.6.6... Installing RDoc documentation for actionpack-3.0.7... Installing RDoc documentation for arel-2.0.10... Installing RDoc documentation for activerecord-3.0.7... Installing RDoc documentation for activeresource-3.0.7... Installing RDoc documentation for mime-types-1.16... Installing RDoc documentation for polyglot-0.3.1... Installing RDoc documentation for treetop-1.4.9... Installing RDoc documentation for mail-2.2.19... Installing RDoc documentation for actionmailer-3.0.7... Installing RDoc documentation for thor-0.14.6... Installing RDoc documentation for railties-3.0.7... Installing RDoc documentation for rails-3.0.7...