> brew install openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
Already downloaded: /Users/administrator/Library/Caches/Homebrew/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Pouring openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

Generally there are no consequences of this for you. If you build your
own software and it requires this formula, you'll need to add to your
build variables:

    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include

> brew link --force openssl
Warning: Refusing to link: openssl
Linking keg-only OpenSSL means you may end up linking against the insecure,
deprecated system version while using the headers from the Homebrew version.
Instead, pass the full include/library paths to your compiler e.g.:
  -I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib

brew update
brew install openssl
ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/

13:22 $ ls -l /usr/local/opt/openssl
lrwxr-xr-x  1 ben  admin  26 May 15 14:22 /usr/local/opt/openssl -> ../Cellar/openssl/1.0.2h_1

brew update
brew install openssl
ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/Cellar/openssl/1.0.2j/bin/openssl /usr/local/bin/openssl

cd /usr/local/src

curl --remote-name https://www.openssl.org/source/openssl-1.0.2h.tar.gz

tar -xzvf openssl-1.0.2h.tar.gz
cd openssl-1.0.2h

./configure darwin64-x86_64-cc --prefix=/usr/local/openssl-1.0.2h shared
make depend
make
make install

ln -s /usr/local/openssl-1.0.2h/bin/openssl /usr/local/bin/openssl

openssl version -a

LDFLAGS=-L/usr/local/opt/openssl/lib
CPPFLAGS=-I/usr/local/opt/openssl/include
PKG_CONFIG_PATH=/usr/local/opt/openssl/lib/pkgconfig
pip install mitmproxy

touch ~/.bash_profile; open ~/.bash_profile

export PATH="$PATH:/usr/local/Cellar/openssl/1.0.2j/bin/openssl"

Jorns-iMac:~ jorn$ openssl version -a
OpenSSL 1.0.2j  26 Sep 2016
built on: reproducible build, date unspecified
//blah blah
OPENSSLDIR: "/usr/local/etc/openssl"

Jorns-iMac:~ jorn$ which openssl
/usr/local/opt/openssl/bin/openssl

brew install openssl
 cd /usr/local/include
 ln -s ../opt/openssl/include/openssl .

brew install openssl
 cd /usr/local/include
 ln -s ../opt/openssl/include/openssl
 ./configure && make

brew install openssl

brew info openssl
echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

brew reinstall ruby
brew reinstall openssl