FIllet Edge

I am curious why this edge causes filletedge so much of a problem. I need a radius of 1-1/2" but unless I get down to 1/4" it fail.

Problem Fillet (84.9 KB)

Hello- I suppose it is that at 1.5 this part of the fillet needs to flip:


Here is something odd I just found
. If I remove the curved edge:

Then fillet edge works but I have to do the entire thing in one operation: