Also, what do you mean with this: "This is because drawing a masked picture into a canvas doesn't erase the background behind the masked areas which is proper behavior." If you mean that the background should be erased if you draw a mask to it, I think you're wrong. The whole point of a mask is to not affect anything in the masked area. If you wan't this behaviour you can use Canvas.ClearRectinstead of Canvas.Refresh. This is also what I would do.
Yes, you are correct. This is the behaviour it should do. We just have to be conscious of it.
So, what I'd do: When you draw a shadow, keep track of the X,Y,Width and Height (store in an array or something). When you are going to draw the next shadow, call Canvas.ClearRect(X,Y,Width,Height) first, then draw the shadow.
That's one solution. Unfortunately it caused flickering without a viable doubler buffering option (which I'll post about shortly). And it clears it to the window background colour which may not be desired if you are not on flat background.
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