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  amp  amp  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

User · Answer

install port  https   guide macports org  install or upgrade openssl package  sudo port install openssl or sudo port upgrade openssl that s it  run openssl version to see the result

User · Answer

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

User · Answer

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

User · Answer

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

User · Answer

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

User · Answer

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

User · Answer

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

User · Answer

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

[macos] Update OpenSSL on OS X with Homebrew

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