I have Ruby 1.8.7, Gems 1.3.5, Rails 2.3.4, OpenSSL 0.9.8k installed on a Solaris machine.
I have tried using the extconf.rb in ruby/ext/opennsl, but I get this: checking for openssl/ssl.h... no
Maybe you need to tell extconf where you ssl stuff is. You should be able to do something along the lines of
ruby extconf --with-openssl-include=/path/to/openssl/headers --with- openssl-lib=/path/to/openssl/libraries
Fred