Why does clear out a pocket says there is nothing to carve

I have a jpg image that I want to use to clear out a pocket from a piece of wood. It can simulate on cut on shape path and inside or outside but not clearing out a pocket. the attached image also show the easel setup. is there a way I can do this?

The object is a ring, and to work the way you want it to work you need a perimeter only.
You would achieve this by coloring the entire shape in before inporting it.
Or this method to fix it after import.

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