Was updating one server with rails 2.2.2 to rails 2.3.8. I upgraded ruby from 1.8.6 to 1.8.7 and also rubygems to 1.3.4 version from a source. When i did ruby script/server to start the server I got this error no such file to load — openssl
After a 15 mins R&D i found that this usually happens on an Ubuntu machine (which it was in my case). The solution is as follows
First install libssl using
sudo apt-get install libssl-dev
Than go to the source of ruby and go to the following path
Run the command one after the others.
sudo make install
Now try to do ruby script/server again……and boooooooom! solved.. Even after trying this you are stuck let me know I shall help you out.