Update OpenSSL on OS X with Homebrew

Question

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:

Answer 1

I had this issue and found that the installation of the newer openssl did actually work, but my PATH was setup incorrectly for it -- my $PATH had the ports path placed before my brew path so it always found the older version of openssl.

The fix for me was to put the path to brew (/usr/local/bin) at the front of my $PATH.

To find out where you're loading openssl from, run which openssl and note the output. It will be the location of the version your system is using when you run openssl. Its going to be somewhere other than the brewpath of "/usr/local/bin". Change your $PATH, close that terminal tab and open a new one, and run which openssl. You should see a different path now, probably under /usr/local/bin. Now run openssl version and you should see the new version you installed "OpenSSL 1.0.1e 11 Feb 2013".