All of the roles that the product should bestow do show up in the uc_roles_expiration_table for the user that purchased the product.

I've peeked into the raw data on the db... the desired roles appear to show up everywhere with the exception of the users_roles table for Drupal. And since the roles aren't bestowed in users_roles, no standard scripting will be able to verify the roles without a query hack.

So to Drupal, the roles don't exist. The role subsystems and Ubercart sees them and assigns them correctly, but the link between Ubercart and the users_roles appears to be buggered somehow.