Recompiling/reinstalling Ruby 2.0 with openssl

Question

I'm currently trying to install gitlab on a fresh Ubuntu server in the rackspace cloud, and this requires I install Ruby 2.0.

So I downloaded ruby via curl and installed it by doing the following:

./configure
make
make install

Then, when trying to install a gem I got an error saying cannot load such file -- openssl.

Clearly I was missing open ssl. So I installed openssl and libssl-dev, as I heard you need this too if you're using Ubuntu:

apt-get install openssl
apt-get install libssl-dev 

I then reinstalled ruby by repeating the steps above:

./configure
make
make install

However, after all of this, I still get the same openssl error: cannot load such file -- openssl

I assume that I'm not reinstalling ruby correctly. There must be some steps I'm missing to remove the initial configuration, however no amount of googling yields an answer that makes sense to me. Does anyone know how I would go about doing this?

edit: I'm downloading ruby from the following source: ftp://ftp.ruby-lang.org/pub/ruby/2.0/ruby-2.0.0-p247.tar.gz

Answer 1

I did that on a standard debian 7, with a fresh openssl installed under /opt/openssl, like this

$cd ~/ruby-src 
$./configure --prefix=/opt/ruby --without-openssl
$make
$sudo make install

And then using ext/openssl/

$export PATH=/opt/ruby/bin:/opt/openssl/bin:$PATH
$which ruby
/opt/ruby/bin/ruby
$which openssl
/opt/openssl/bin/openssl
$cd ~/ruby-src/ext/openssl/
$ruby extconf.rb --with-openssl-dir=/opt/openssl
$make
$sudo make install

I had to comment out the line with OP_MSIE_SSLV2_RSA_PADDING in ossl_ssl.c, because that constant does not exist in the current openssl distribution, but then everything compiled cleanly.