The version of OpenSSL that comes with your Mac system is as follows
$ OpenSSL versionopenssl 0.9.8zh Jan 2016
Check the latest version on GitHub
Installing OpenSSL with homebrew
Brew Install OpenSSL
If the version of OpenSSL differs significantly from the new version, it needs to be reinstalled after homebrew.
Homebrew default installation path is as follows
/usr/local/cellar/openssl
There are some permissions issues with the system's own OpenSSL, so it cannot be deleted. In order to use the newer version of OpenSSL properly, you can use the homebrew installed OpenSSL to make aliases (i.e., shortcuts), move to use the location double-click Open.
This version of OpenSSL is shown as 1.0.2h_1. Exit command is exit (can also be exited directly)
Ok.
Resources
Mac OSX EI Capitan 10.11.6 upgrade comes with OpensslMac10.11 upgrade install OpenSSL
Mac upgrade OpenSSL