Can't quite work out cleanly filetting inside corners

I have a simple 4" circle and slightly smaller square. I extrude & cap them, then boolean union.

However, I can’t seem to work out how to get a clean “actual” fillet, and it doesn’t work with edge softening, either… not sure what I should be doing differently.

I’ve tried this a few different way, but the fillet geometry for the inside corner where the circle meets the square is always “broken” - sometimes, also missing a few faces. (I’ve tried re-capping and that works, but the edge always breaks again when filleting.

Hello - how does the wireframe look? FilletEdge on all vertical and top edges should get you something like this:


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Seems to be working now.