Hi Brian, your handle is kind of just skimming along the outer edge of your cup body, it isn't sticking all the way through it.
Zooming in on this area:
You can see that there is some space between the handle and the body:
Zoom in to that area and then drag the handle over a little bit so that it is sticking through there a little bit, best is so that it is about half-way through the wall of the body, like this:
After that the boolean should work fine, and then a fillet will work up to about a max of 0.45 radius:
Let me know if you have any more problems with it!
- Michael
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