For resolving OCSP Status Request extension unbounded memory growth (CVE-2016-6304) on macOS Sierra using brew with System Integrity Protection enabled:

1. Temporarily adjust permissions on /usr/local so brew can update

    sudo chgrp -R admin /usr/local
    sudo chmod -R g+w /usr/local
   

2. Install the updated version of OpenSSL (probably 1.0.2i is what you want)

    brew install openssl
   

3. You may want/need to delete an existing symlink to openssl from /usr/local/bin:

    rm /usr/local/bin/openssl
   

4. Re-link the proper brew version:

    sudo ln -s /usr/local/Cellar/openssl/1.0.2i/bin/openssl /usr/local/bin/openssl
   

5. Restore original permissions on /usr/local/bin:

    sudo chown root:wheel /usr/local
   

For resolving OCSP Status Request extension unbounded memory growth (CVE-2016-6304) on macOS Sierra using brew with System Integrity Protection enabled:

1. Temporarily adjust permissions on /usr/local so brew can update:

    sudo chgrp -R admin /usr/local
    sudo chmod -R g+w /usr/local
   

2. Install the updated version of OpenSSL (you probably want 1.0.2i):

    brew install openssl
   

3. You may want/need to delete an existing symlink to openssl from /usr/local/bin:

    rm /usr/local/bin/openssl
   

4. Re-link the proper brew version:

    sudo ln -s /usr/local/Cellar/openssl/1.0.2i/bin/openssl /usr/local/bin/openssl
   

5. Restore original permissions on /usr/local/bin:

    sudo chown root:wheel /usr/local