Has anybody tried this, and were you successful?

I have this simple tabard, I suppose you'd call it, made from a flat plane. That was draped in the cloth room, exported and used as the cloth for the next step. A simple belt shrinks during the simulation, the intention being to gather the tabard in around the waist. But no matter what I do, the tabard always passes through the belt.

I've tried different collision settings, and different cloth settings, with no joy.

In the animation above, the belt is at its final size at the end of the simulation, and you can see that the cloth hasn't settled fully. So I tried another run, with a lot of settling frames after the belt finishes shrinking, and in that one the tabard passed right through the belt and returned to its original shape. :(

Any ideas?