Correctly upgrading ruby on MS Windows

Hi, I am looking for some guidance on the correct and/or most streamlined way to upgrade Ruby. Presently I am on Ruby version 1.8.6 patch level 111. I am looking to upgrade to version 1.8.6 patch level 287. When I tried downloading the ruby-1.8.6-p287-i386-mswin32.zip file I unzipped it and was optmistically hoping that i could take all of its files and overlay my current installation. When I checked the rails version with (rails -v), I get the following error: D:\Mercury\GreenLight\server>rails -v c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:713:in `set_paths': undefined method `uid' for nil:NilClass (NoMethodError)         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:711:in `each'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:711:in `set_paths'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:518:in `path'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems/source_index.rb: 66:in `installed_spec_directories'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems/source_index.rb: 56:in `from_installed_gems'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:726:in `source_index'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:138:in `activate'         from c:/ruby/lib/ruby/site_ruby/1.8/rubygems.rb:49:in `gem'         from c:/ruby/bin/rails:18

I also saw that ruby/script console and ruby script/server -e commands also failed. I've tried renaming the current c:\ruby directory and just creating ane c:\ruby directory with just the patch level 287's contents and that fails because some of the binaries are missing. Which gems and/or plugin require reinstallation after a correct upgrade? Please advise?