Update OpenSSL on OS X with Homebrew

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:

brew install openssl
brew link openssl --force

Nevertheless, it does not work:

openssl version
OpenSSL 0.9.8r 8 Feb 2011

brew unlink openssl && brew link openssl --force
Unlinking /usr/local/Cellar/openssl/1.0.1e... 1139 links removed
Linking /usr/local/Cellar/openssl/1.0.1e... 1139 symlinks created

The SVN issue is not resolved either. Any ideas? I would rather not try the MacPorts way because it may interfere with Homebrew.

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.

installed openssl on mac with brew but nothing found on /usr/local/bin where other brew installed bins are located. Found my fresh openssl here:

/usr/local/opt/openssl/bin/openssl

Run it like this:

/usr/local/opt/openssl/bin/openssl version

I don't want to update OS X openssl, while some OS stuff or other 3rd party apps may have dependency on older version.

I also don't mind longer path than just openssl

Writing this here for all the Googlers who are looking for location of openssl installed by brew.

In a terminal, run:

export PATH=/usr/local/bin:$PATH
brew link --force openssl

You may have to unlink openssl first if you get a warning: brew unlink openssl

This ensures we're linking the correct openssl for this situation. (and doesn't mess with .profile)

Hat tip to @Olaf's answer and @Felipe's comment. Some people - such as myself - may have some pretty messed up PATH vars.

I had this issue and found that the installation of the newer openssl did actually work, but my PATH was setup incorrectly for it -- my $PATH had the ports path placed before my brew path so it always found the older version of openssl.

The fix for me was to put the path to brew (/usr/local/bin) at the front of my $PATH.

To find out where you're loading openssl from, run which openssl and note the output. It will be the location of the version your system is using when you run openssl. Its going to be somewhere other than the brewpath of "/usr/local/bin". Change your $PATH, close that terminal tab and open a new one, and run which openssl. You should see a different path now, probably under /usr/local/bin. Now run openssl version and you should see the new version you installed "OpenSSL 1.0.1e 11 Feb 2013".