I\'m using MacOS X 10.7.5 and I need a newer OpenSSL version due to handshake failures. There are several tutorials on the internet and I tried the following:
To answer your question regarding updating openssl I followed these steps to successfully update the version found on my Mac to the newest openssl version 1.0.1e.
I followed the steps found here: http://foodpicky.com/?p=99
When you reach the steps for terminal commands make and make install be sure to use sudo make and sudo make install (I had to go through the step-by-step twice because I did it without sudo and it did not update).
Hope this helps