If you got something similiar while to, while compiling Ruby 1.9 from MacPorts, and have latest openssl library (1.0.0a):

“/opt/local/var/macports/build/-opt-local-var-macports-sources-rsync.macports.org-release-ports-lang-ruby19/work/ruby-1.9.1-p429” && /usr/bin/make -j2 all ” returned error 2 :error:build Target org.macports.build returned: shell command failed

You should:

1. Set up a local port repository. In the file

   /opt/local/etc/macports/sources.conf
   

   add this line before the rsync line:

   file:///Users/Shared/dports
   

2. Run:

   mkdir -p /Users/Shared/dports && cd /Users/Shared/dports && svn co --revision 69417 http://svn.macports.org/repository/macports/trunk/dports/devel/openssl/ devel/openssl/
   

3. Re-index Portindex:

   portindex /Users/Shared/dports
   

4. You got it, just do:

   port install ruby19
   

   if you don’t want suffix at then end of ruby binary, use:

   port install ruby19 +nosuffix
   

This will install ruby + openssl 0.9.8a and ruby will be fine ;)