I think that the magnification is so small that it would take a long distance for this to happen. The point of glasses is to bend the light just enough that the lens in the eye can focus the images comfortably, without strain. The focus would be moved on the order of millimeters or less.
The only way that this image flip could happen, in my mind at least, is for the person to be nearly legally blind, and you seeing the image with the glasses 5+ feet away.
One more point to add: Were the glasses for someone near or far-sighted? If I have my facts straight, someone near sighted would never have the flip (concave lenses) and far sighted might, under extreme circumstances. (convex)
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