mxcl/homebrew — Issue #10577: brew should begin to require its own OpenSSL with lion and beyond
Author: dwaite
Created: 2012-02-28 23:48:04+00:00
State: open

Apple has as of Lion deprecated the use of the system openssl, which will eventually be removed.

http://ludovicrousseau.blogspot.com/2011/08/mac-os-x-lion-and-openssl.html

My understanding is this is due to binary backwards incompatibilities in the openssl library across minor/maintenance versions (most probably due to direct access of structure data). This has prevented upgrades beyond 0.9.8r. The recommendation is to use common crypto or link against your own build of openssl.