Hi ndrakey, is it possible for you to post the 3DM model file so I could examine the 9 more closely? It's not too unusual for fonts to have messy structures in them like little segments that are not totally smooth to the surrounding curves. It's difficult to notice something like that when the font is used for 2D print purposes but filleting is a lot more sensitive than that.

Also it may just be that the sharpness of the shape there is a problem, it might help if you would also fillet the vertical edge going downwards from the 9 in that spot to make it easier for the fillet to form a corner patch in that spot.

I could probably give you more information if I could examine the actual model though.

- Michael