Install OpenSSL from source Mac OS X

install-openssl-from-src-mac

# Install older OpenSSL 1.0.0 from source on Mac OS X to install Ruby version compatible (like 1.8.7)

# prepare workspace
mkdir -p ~/code/build-from-src/ && cd $_

# download source code
curl -LO https://www.openssl.org/source/openssl-1.0.0.tar.gz

# expand tar
tar -xzvf openssl-1.0.0.tar.gz
cd openssl-1.0.0

# dependencies
brew install makedepend
make depend

# configure, make, install
perl ./Configure --prefix=/usr/local --openssldir=/usr/local/openssl no-ssl3 no-ssl3-method no-zlib darwin64-x86_64-cc enable-ec_nistp_64_gcc_128
make
make test
sudo make install MANDIR=/usr/share/man MANSUFFIX=ssl

# verify
openssl version
which -a openssl

# clean up
make clean
make distclean
cd ..
rm -fr openssl-1.0.0
rm openssl-1.0.0.tar.gz