I tried using polygons (which I normally use) and regions and only regions gave me something. But I think I know what's going on:
If understand it correctly, only polygons obey cutouts and keepouts etc, regions do not.
So the shape I was converting would never fill with copper when using polygons but worked fine with regions.
Now I know- the shape was too close to board edge, so polygons would respect design rules and refuse to work, while regions did not.
And of course cutouts are essentially the same thing as design rules..