An application currently running with jruby 1.5.0 and rails 2.3.8 shall be upgraded to jruby 1.6.8 and rails 3.2. Attached is the report generated by the rails_upgrade plugin. We provide assistance to the developer with a test environment and help when installing/configuring/testing the application. Code quality is a priority (no quick and dirty approach).
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Do you have any tests? This would greatly increase the ease of upgrading. :) That said, I have upgraded apps from 2.3 to 3.0, and from 3.0 to 3.1. I also have some experience with jruby.