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So here's the problem.

1. I want to have two objects overlapping. I want the shadow from the top object to shadow the lower object.

2. The diagram is of a very complex taxonomy tree. It is set to auto layout and branches tend to get re-arranged a lot. The objects on top are small badges or labels attached to the taxonomy item. They have to move with those items

3. So you group the badge with the item - no, the badge's shadow doesn't appear on the lower taxonomy shape.

4. So you move the badges to a separate higher layer. Now you can no longer group them with the shapes underneath.

Any answer to this condundrum?