Hi Brian, sometimes the filleter will get confused when extra edges are thrown into the mix.
For the side piece, instead of having it in 2 pieces it would probably work better if it was all one big plane.
To do that here, I would select these 2 faces:
Then just delete them, leaving a hole there:
Then select that and use Construct / Planar to build a single plane end cap there:
Repeat this with the opposite side and the adjacent small edge (a separate pass for each), which are made up of 2 pieces. A single large plane is much more likely to make the filleter happy. But you're best off doing this procedure to the original shape before any fillets were applied at all.
Every time there is a juncture with many edges coming together, it makes the filleter have to do much more analysis for trying to figure out how to place a corner in that area.
If you are still stuck and have the original unfilleted version, please post that and I'll check it out some more.
- Michael
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