I had a hard time updating openssl on my Mac OSX. Here’s what I did to update the libraries:
Install and upate brew
brew update brew install openssl brew link --force openssl
If one of the bad versions come up (1.0.1a-f), you can figure out which version of openssl you’re using, this way:
Often this is from /usr/bin. To make sure you get the updated version, drop a symlink into /usr/local/bin to point to the updated openssl, like this:
ln -s /usr/local/Cellar/openssl/1.0.1g/bin/openssl /usr/local/bin/openssl
Note: You may have to exit and start the Terminal session to see the new changes.
As an alternative to that final step, some people replace the openssl in /usr/bin with a symlink to /usr/local/Cellar/openssl/1.0.1g/bin/openssl (or whatever your version is):
mv /usr/bin/openssl /usr/bin/openssl_OLD
ln -s /usr/local/Cellar/openssl/1.0.1g/bin/openssl /usr/bin/openssl
But this is known to cause problems with some more recent versions of OSX. Better to just insert a new symlink into /usr/local/bin, which should take precedence on your path over /usr/bin.