Environment:
ubuntu 10.04
eclipse 3.6.1
ruby v1.9.2p0 (install from source)
ruby plung-in: Aptana
Steps:
1. eclipse Debug Configuration. interpreter -> local (it seems eclipse only suppor ruby 1.8 debug. not sure)
2. install openssl and libssl-dev on ubuntu (from ubuntu software center).
3. compile ruby with openssl support
$>cd [ruby_source_floder]/ext/openssl
$>ruby extconfig.rb
$>make
$>sudo make install
4. install ruby-debug
$>sudo gem install ruby-debug19
$>sudo gem install ruby-debug-ide19