Update OpenSSL on OS X with Homebrew

Question

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.

Solution 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 2

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 3

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 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 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

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Comments

[netwire]

Thanks, that worked. I reference this doc on how to add to $PATH: hathaway.cc/2008/06/…

[Yavor Ivanov]

Thanks! Killed couple of hours on this issue.

[Felipe]

In my case I put this on my ~/.profile PATH=/usr/local/bin:/usr/bin:/bin:/usr/sbin:/sbin:/usr/local‌​/bin:/opt/local/bin:‌​/opt/local/sbin:/opt‌​/X11/bin:/usr/local/‌​MacGPG2/bin:/usr/bin‌​:/bin:/usr/sbin

[SapphireSun]

FYI as of today, 1.0.1e (specifically 1.0.1a-f) is known to have a serious security vulnerability. Future readers, make sure you upgrade to at least 1.0.1g heartbleed.com

[quantumpotato]

The old version is still showing for me: stackoverflow.com/questions/22974590/…

[jww]

Minus One: "... be sure to use sudo make..." - You don't make with privileges. You just make and and then sudo make install if needed. You also cited a horrible reference. It replaces Apple's OpenSSL 0.9.8 in /usr with the updated 1.0.x. That's a really bad thing to do because there's no binary compatibility.

[Peyman Mohamadpour]

I have installed 1.0.2h_1, but I am exactly on the same situation, but openssl version -a still gives me OpenSSL 0.9.8zg 14 July 2015. Any suggestions?

[biplob]

Exactly same thing happened to me. It's fixec by @Marc Smith answer

[Timo]

This one doesn't work because brew link --force openssl Warning: Refusing to link: openssl Linking keg-only openssl means you may end up linking against the insecure, deprecated system OpenSSL while using the headers from Homebrew's openssl. Instead, pass the full include/library paths to your compiler e.g.: -I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib

[Tuhina Singh]

@TimoLehto Were you able to resolve this issue? Am facing same issue and cant seem to find a solution anywhere

[Timo]

@TuhinaSingh Sorry no luck, other than "following the instructions" and not linking the system library, but instead linking on demand with flags whenever I need it for compile or just calling the brew version directly i.e. /usr/local/Cellar/openssl/1.0.2h_1/bin/openssl

[Wade Williams]

The question was about Homebrew... macports is not homebrew... The OP states they prefer not to use mac ports.

[Morteza Sepehri Niya]

@WadeWilliams mac in new version dose not let you update openssl using Homebrew, I mean you can install or update it using Homebrew but you can not prioritize it. So, instead of updating it using Homebrew you can update it using macports and prioritize it.

[brunodd]

@TimoLehto No idea if this is 'good practice' or even safe to do, but you could always create a link from /usr/local/bin to /usr/local/opt/openssl/bin/openssl. This can be done using the following command: ln -s /usr/local/opt/openssl/bin/openssl /usr/local/bin/openssl. To be clear: I can't promise you that this is a safe or correct way of proceeding.

[ekkis]

more info on this issue: stackoverflow.com/questions/38670295/…

[rogerdpack]

It just says Refusing to link: openssl