When I run brew doctor in Terminal: I get the following error:
Warning: Some keg-only formula are linked into the Cellar.
You may wish
Hengjie is half way there.
The problem is that OSX ships with a version of openssl in /usr/bin. Try this:
$ /usr/bin/openssl version
When homebrew installs openssl it will install it to /usr/local/Cellar/openssl, but by default it won't create the links because of the version conflict that it would create. To crete the links you need to type in:
$ brew link --force openssl
That will create symlinks to the brew version and you should be able to see the new version number by typing this:
$ /usr/local/bin/openssl version
There is one final problem. And that happens if your path variable has /usr/bin ahead of /usr/local/bin. Type this in:
$ echo $PATH
if you see /usr/bin ahead of /usr/local/bin then you need to update your .bash_profile to have something like this in it:
export PATH="/usr/local/bin:$PATH"
That will mean that the new version will be used ahead of the old one.
Warning: the brew package says this "Mac OS X already provides this software and installing another version in parallel can cause all kinds of trouble."
So use at your own risk! I don't actually know what the "all kinds of trouble" is.