It's been just over 24 hours since I manually awarded the bounty on my question.
This is the first bounty that I've set and awarded on Meta, but I haven't gotten the Benefactor badge yet. Obviously, I don't care much about the badge itself; I want to make sure the system is working properly.
I'm uncertain how isolated this is. I don't think it's a Trilogy-wide problem as it was awarded once (at the time of writing) on Stack Overflow after the initial round of awardings. I checked and I'm not in the list on Meta (just in case the system thinks I have the badge).