I noticed this, same happens in every application, including the widget gallery. Notice how the tips update every time I press the button, but the button seems to only show the depressed state once every N number of clicks (or so it seems).
Might be related to me clicking fast enough for it to consider it a double-click.
Added some log statements, seems like by the time the paint event is dispatched the mouse-up event had already been dispatched:
Serendipity(31): down: 0x04684818
Serendipity(31): button paint 0x04684818 pressed: true
Serendipity(31): up: 0x04684818
Serendipity(31): button paint 0x04684818 pressed: false
Serendipity(31): down: 0x04684818
Serendipity(31): up: 0x04684818
Serendipity(31): button paint 0x04684818 pressed: false
Serendipity(31): down: 0x04684818
Serendipity(31): up: 0x04684818
Serendipity(31): button paint 0x04684818 pressed: false
Serendipity(31): button paint 0x04684818 pressed: false
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