DeskTask Transparent abilities and ClearType (found on Windows XP Systems) don't combine well.

ClearType cleans the edges on fonts to blend with the background and this is where DeskTask as problems, it as no fixed background, so sometimes it looks good, but sometimes you will see shades of black.
Also ClearType is automatic, there is no way a programmer can say to Windows : "Don't draw this text with Clear Type".

So the only Workaround, besides turning off cleartype, is using a bitmap font (ClearType only works on True Type Fonts). Bitmap fonts are pixel basead fonts instead of vector based like the True Types one. That is the reason why a bitmap font only one fixed size (some may have severall sizes, but different font files have to be installed. True Type fonts supports all sizes in the same file).

There are a lot of free bitmap fonts on the web, it's just a question of finding one that suits you.



In this screenshot I used this font which is a bit small but looks good on any background, and even better with shadow on.