ijy1001

It doesn't make any difference for me whether it's set to winding or alternate. It seems like there must be some problem beyond the fill mode as In some cases the shapes created are completely the wrong outline, or missing parts of the path they should have (e.g. in the example I posted the letters have no internal path for the negative space once merged) . Also as mentioned Designer crashed to desktop at one point after clicking the add button.

Booleans seem to frequently give wrong results when shapes made by converting text to curves, for example: Text converted to curves and duplicated: Shape after boolean add operation: The issue seems to be worse with letters that have curved lines, straight edges work more reliably. Problems range from inner holes being filled in, as above, to the majority of the shapes being deleted apparently randomly. On one occasion while testing the software crashed to desktop.