From: Jeremy Kemper <jeremy@...>
Date: 2013-02-28T00:27:36+09:00
Subject: Re: Mac OS 10.8.2 and openssl

On Wed, Feb 27, 2013 at 3:32 AM, Dr. Hegewald <hegewald@irmb.tu-bs.de> wrote:
> ERROR:  Loading command: install (LoadError)
>         cannot load such file -- openssl

Take a look at ruby-build. It handles the ins & outs of compiling Ruby
on the Mac, including OpenSSL:
https://github.com/sstephenson/ruby-build

Otherwise, you'll need to build openssl, configure Ruby
--with-openssl-dir, and fetch your own root CA certificates. Big song
and dance.

RVM can wrap this up for you, too: https://rvm.io/rvm/install/

(I wish Ruby kept support for Apple's patched OpenSSL, even though
it's deprecated and broken.)