This has something to do with transparency. In fact drawing with ClearType does not make sense on a transparent canvas. But this should be handled and draw normal antialiasing instead in this case.
The rectangles you see are font overhang, i.e, where text may go out of its box, for example with italic style.
I've made some filters in LazPaint to simulate ClearType. It's on subversion. So you can take an image or a screenshot that does not have ClearType and apply it, or the contrary, take a screenshot and remove ClearType effect afterwards.