I've run into a similar issue, but rather than being rotation related it seems to be affected by the position of the shape being added.
In the first two screenshots I've attached, if I try to individually add each of the circles to the diamond, they all work except for the top-right one. If I move the circle to one of the other sides of the diamond, it adds fine. Also if regardless of where the circle is (even in the problem area) if I select all objects at once and add then it works fine.
It doesn't seemt o be the whole top-right quadrant of the shape however, if move the circle up along 45 degrees, there is a point where it starts to add correctly (see the last two screenshots).