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:
If you're using Homebrew /usr/local/bin should already be at the front of $PATH or at least come before /usr/bin. If you now run brew link --force openssl in your terminal window, open a new one and run which openssl in it. It should now show openssl under /usr/local/bin.