1. Install Ruby One Click installer containing rubygems 0.9.4

At this point, rubygems work fine, gems can be installed, updated, etc/

2. Upgrade rubygems to version 1.1.0 by gem update --system.

Attempting to install a gem now raise "Errno::ECONNABORTED: An established connection was aborted by the software
in your host machine. reading http://gems.rubyforge.org/gems/pathname2-1.5.2.gem"

I have verified this multiple times, 0.9.4 works fine, 1.1.0 never works. The machine is running XP SP2 with all updates
installed. No firewall or antivirus enabled AFAIK.

Attaching log with output  --debug

RubyGems Environment:
 - RUBYGEMS VERSION: 1.1.0 (1.1.0)
 - RUBY VERSION: 1.8.6 (2007-09-24 patchlevel 111) [i386-mswin32]
 - INSTALLATION DIRECTORY: c:/ruby/lib/ruby/gems/1.8
 - RUBY EXECUTABLE: c:/ruby/bin/ruby.exe
 - RUBYGEMS PLATFORMS:
   - ruby
   - x86-mswin32-60
 - GEM PATHS:
    - c:/ruby/lib/ruby/gems/1.8
 - GEM CONFIGURATION:
    - :update_sources => true
    - :verbose => true
    - :benchmark => false
    - :backtrace => false
    - :bulk_threshold => 1000
    - :sources => ["http://gems.rubyforge.org", "http://gems.rubyonrails.org"]
 - REMOTE SOURCES:
    - http://gems.rubyforge.org
    - http://gems.rubyonrails.org

Date: 2008-04-07 21:59
Sender: Eric Hodel

Fixed.

Date: 2008-04-04 15:45
Sender: Luis Lavena

RubyGems 1.1.0 got out with an error into RemoteFetcher that
don't catch the exception you're getting.

This is fixed in trunk and will be available in the next
release.

You can downgrade to 1.0.1 with:
gem update --system -v '1.0.1'