Thanks for the clarification, @netabreuer , and the model. I guess the short answer here is: This is a legitimate Fillet failure case. If you turn on Curvature Comb analysis for this model, you can see that there are areas of very high curvature at the bottom corners:


And, those will always cause Fillet failures. Further, you can see as you increase the Fillet radius, the geometry in those corners gets strange:

Which, I think, is an early indication that this is a problem area for Fillet.
As to what to do: @TrippyLighting is right - possibly a different workflow is needed - perhaps a different way to do that front/back cut that doesn't result in such high curvature, or adding this geometry in the T-Spline model, or even modifying the T-Spline, or the sketch, to get a result that is more easily Filleted. You could possibly use a different type of Fillet as well. Perhaps you could define a Variable Radius fillet that has a smaller radius in the area of high curvature would help.
Jeff Strater
Engineering Director