you linked against the wrong openssl lib you need to run something like this: (for rvm) otool -L ~/.rvm/rubies/ruby-1.9.3-p0/lib/ruby/1.9.1/x86\_64-darwin11.2.0/openssl.bundle (for rbenv) otool -L ~/.rbenv/versions/1.9.3-p0/lib/ruby/1.9.1/x86\_64-darwin11.2.0/openssl.bundle if you have any references to /opt or any non-osx openssl lib (say from brew) you are F\*\*\*\*\* and will need to rebuild ruby. this is the source of the ssh/http/and random seg faults you've been having on various projects.
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