First of all, you need ‘brew’ (http://brew.sh/)

$ brew update
$ brew install openssl
$ brew link --force openssl
 
$openssl version -a

If it’s still the old version, you shoud:

$ sudo rm /usr/bin/openssl  #remove the old binary 
$ sudo ln -s /usr/local/Cellar/openssl/1.0.1h/bin/openssl /usr/local/bin
(1.0.1h -> the latest version)

ref: http://apple.stackexchange.com/questions/126830/how-to-upgrade-openssl-in-os-x

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