@Marc One distinction that I forgot to mention is that I am using ruby
1.9.2 (from either rbenv or rvm). Here are the following situations
where the script works and fails.

Ubuntu 12.04 + openssl in updates + stock ruby 1.8.7: Pass
Ubuntu 12.04 + openssl in updates +  compiled ruby 1.9.3: Fail
Ubuntu 12.04 + openssl manually installed from ubuntu 11.10 + compiled ruby 
1.9.3: Pass

There is some specific problem with the latest openssl and ruby 1.9.3.

as Adam said "Otherwise, the choice
seems obvious to me: disable TLS 1.1 and 1.2 by default so that Ubuntu
users who have upgraded to "Precise 12.04 Long Term Support" will not
have their software mysteriously fail without recourse."

This is what happened to me. I upgraded a server from 11.10 to 12.04 to
get on a recent LTS release. Next thing I know credit card processing is
failing. It took me a long time to track down that the new openssl libs
were the problem. Now that I know i can manually downgrade them.
However, problems like this should not magically pop up.

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https://bugs.launchpad.net/bugs/965371

Title:
  HTTPS requests fail on sites which immediately close the connection if
  TLS 1.1 negotiation is attempted, on Ubuntu 12.04

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