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Install Openssl From Source + Ruby - Debian

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//build essentials + extras (last line not needed)
sudo aptitude install ssh gcc sudo build-essential make git-core subversion -y
sudo aptitude install bash man-db cron wget lynx bind9 -y
sudo aptitude install mysql-server mysql-client libmysqlclient15-dev libmysql-ruby sqlite3 imagemagick -y

//When doing ./configure --with-openssl=/dir where /dir is some valid directory that contains lib/ file
find / -name

//so replace with...
./configure --prefix=/usr/local --with-openssl-dir=/usr/lib


find / -name*
/usr/lib as ln -s

----ignore---- debian don't like you doing the below

//beforehand, kill off any existing openssl copy
sudo aptitude remove openssl
rm -rf /usr/bin/openssl
which openssl

//now compile & install a new copy of openssl from source
cd /usr/src
tar xzf openssl-0.9.8h.tar.gz
cd openssl-0.9.8h
./config --prefix=/usr
sudo make
sudo make test
sudo make install

----ignore---- debian don't like you doing the above

//now ruby 1.8.6 from source + openssl support
cd /usr/src
tar xfz ruby-1.8.6-p114.tar.gz
cd ruby-1.8.6-p114
./configure --prefix=/usr/local --with-openssl-dir=/usr/lib
sudo make 
sudo make install

//now gems from source
cd /usr/src
tar xfz rubygems-1.2.0.tgz
cd rubygems-1.2.0
sudo ruby setup.rb

//update with
sudo gem install rubygems-update
sudo update_rubygems

...more here