Ruby on Rails

I'm having a tough time tracking down why my mail is not being sent from an app I migrated from 3.0 -> 3.1 -> 3.2. The relevant code sections are in this SO question. My questions here are:

1) Does something just jump out as wrong in my setup?

2) How would you track this down. All my specs pass and all my cuke scenarios pass and they really pound on the mail.

Thanks!