Hi Branden, or also if you include that front edge to be filleted and then enable the "Straight corners" checkbox in the fillet options (which tries to intersect fillets directly with each other instead of building corner patches), you will get a more complete fragment and you can see where the filleter is failing, it's not able to get this area here:



To use this partial result, you'll accept the fillet partial result, select it and use Ctrl+C to copy it to the clipboard, then undo to restore your main object, then delete the inset faces, then Ctrl+V to paste in the partial result. Then the tricky part is to get the corners filled in with pieces that will make it possible to trim the excess area of the main surface by the fillet piece.

- Michael