building ruby with a specific openssl

ruby-openssl-build.sh

#!/bin/sh

t_dir="$HOME/tmp"

mkdir -p ${t_dir}
pushd ${t_dir}

for url in \
    ftp://ftp.ruby-lang.org/pub/ruby/ruby-1.9.3-p194.tar.bz2 \
    http://openssl.org/source/openssl-1.0.1c.tar.gz
do
  if [ ! -f $(basename "${url}") ] ;then
    wget "${url}"
  fi
done

tar zxf openssl-1.0.1c.tar.gz
tar jxf ruby-1.9.3-p194.tar.bz2

cd ${t_dir}/openssl-1.0.1c
./config \
  no-shared \
  --prefix=${t_dir}/static && \
  make depend && \
  make && \
  make install
  
cd ${t_dir}/ruby-1.9.3-p194
CFLAGS=" -I${t_dir}/static/include -L${t_dir}/static/include " \
LDFLAGS=" -L${t_dir}/static/include " \
./configure \
  --prefix=${t_dir}/static \
  --disable-install-doc && \
  make && \
  make install

${t_dir}/static/bin/ruby -r openssl -e 'puts OpenSSL::OPENSSL_VERSION'

popd

Note that building Ruby with a specific OpenSSL version does not guarantee that Ruby uses the same version during runtime. For this you need to check OpenSSL::OPENSSL_LIBRARY_VERSION. So in the example above, Ruby despite everything uses a shared library from the OS.