Update OpenSSL on OS X with Homebrew

Question or issue on macOS:

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.

How to solve this problem?

Solution no. 1:

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.

Solution no. 2:

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.

Solution no. 3:

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.

Solution no. 4:

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”.

Solution no. 5:

To answer your question regarding updating openssl I followed these steps to successfully update the version found on my Mac to the newest openssl version 1.0.1e.

I followed the steps found here: http://foodpicky.com/?p=99

When you reach the steps for terminal commands make and make install be sure to use sudo make and sudo make install (I had to go through the step-by-step twice because I did it without sudo and it did not update).

Hope this helps

Solution no. 6:

I had problems installing some WordPress plugins on my local server running php56 on OSX10.11. They failed connection on the external API over SSL.

Installing openSSL didn’t solved my problem. But then I figured out that CURL also needed to be reinstalled.

This solved my problem using Homebrew.

brew rm curl && brew install curl --with-openssl

brew uninstall php56 && brew install php56 --with-homebrew-curl --with-openssl

Solution no. 7:

On mac OS X Yosemite, after installing it with brew it put it into

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

But kept getting an error “Linking keg-only openssl means you may end up linking against the insecure” when trying to link it

So I just linked it by supplying the full path like so

ln -s /usr/local/opt/openssl/bin/openssl /usr/local/bin/openssl 

Now it’s showing version OpenSSL 1.0.2o when I do “openssl version -a”, I’m assuming it worked

Solution no. 8:

1. install port: https://guide.macports.org/
2. install or upgrade openssl package: sudo port install openssl or sudo port upgrade openssl
3. that’s it, run openssl version to see the result.

Hope this helps!