From: guillermo haas-thompson <lists@...>
Date: 2013-02-28T09:15:19+09:00
Subject: Re: Mac OS 10.8.2 and openssl

To recap:
• I installed openssl via Homebrew
• I completely removed RVM and went with Chruby
• Was following the instructions for 2.0.0 at
https://github.com/postmodern/chruby/wiki/MRI

In my comment above, where I reference ruby-build issue #305, a user
under that thread said: "configure: WARNING: unrecognized options:
--with-openssl-dir
Confusingly, this is normal. Ruby doesn't recognize the option, but the
openssl extension does."

So, taking a leap of faith and combining that with the Chruby wiki, the
final command that appears to have worked for me is:
./configure --prefix=/opt/rubies/ruby-2.0.0-p0 --with-openssl-dir=`brew
--prefix openssl`   --with-readline-dir=`brew --prefix readline`
--with-yaml-dir=`brew --prefix libyaml`  --with-gdbm-dir=`brew --prefix
gdbm`  --with-libffi-dir=`brew  --prefix libffi`

The trick is to completely ignore the error message spit back from
./configure about not knowing what any of these --with options are and
go ahead with the rest of the instructions on building and installing
the makefile.

Finally, I just cd'd into my app with Ruby 2.0.0 and was able to "gem
install bundler" without getting an openssl failure. First time I tried 
to bundle my gems though, I did get an SSL error.

And finally:
• Got an email back from Postmodern with this lifesaver 
https://github.com/raggi/openssl-osx-ca#readme

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