Issue #863 has been updated by Brian Candler. And I've also just got the same successful result with ruby-1.8.7-p72 on the same platform. ./configure --program-suffix=187 make sudo mv /usr/local/lib/ruby /usr/local/lib/rubyxx sudo make install $ irb187 irb(main):001:0> RUBY_VERSION => "1.8.7" irb(main):002:0> require 'openssl' => true irb(main):003:0> OpenSSL::SSL::VERIFY_PEER => 1 (I'm not sure if there is a clean way to install 1.8.7 alongside 1.8.6. I see ./configure --help shows how to relocate the vendor_ruby and site_ruby directories, but I can't see the same for RUBY_LIB) ---------------------------------------- http://redmine.ruby-lang.org/issues/show/863 ---------------------------------------- http://redmine.ruby-lang.org