Fillet Radius

Trying to make this fillet work. Solid so not sure why it is doing this?

Keep getting this issue of the fillet not connecting.

Probably because of the surface in the corner which does not have an edge being filleted.

Are the top surfaces co-planar? If so then before filleting::

V7: MergeCoplanarFaces or MergeAllCoplanarFaces

V6 and previous: MergeFace or MergeAllFaces

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Thanks David, you were correct. I have not used fillets before and I spent several hours looking for some sort of answer. Most of the videos are basic and do not describe how to handle situations like this.

Thanks again for taking the time to answer my question.