I had this issue with Ginger Newson, but the award did show up in the household inventory a few Sim days later.
Garrett and Gavin were at home, and Garrett got the option to go with or without Gavin. I was going to send Gavin after he completed a task, but once Garrett left, Gavin no longer had the option to go on his own. I thought that was strange, because I've always been able to send household members to religious services on Winterfest separately (if necessary) and the option seems to work the same way.
I just noticed that the whole thing happened on Night on the Town day, if that makes any difference. (This screenshot was taken right afterward - it's a recreation of a family from TS2.)
