I bet this is a dumb question but it’s kicking my butt… How can I get radii to 'over lap" (picture is worth a 1,000 words)
I bet it’s really easy and I am just making it hard! 
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I guess I don’t think it’s terribly difficult but then it kind of depends on the angle you approach it from. Change the order of operations. Radius the vertical edge first. Then you can use Follow Me to sweep a radius around the bottom edges.
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No such thing as a dumb question - of you don’t ask a question, you miss a opportunity to learn.
You could use the FollowMe tool built into Sketchup. Or Fredo’s Round Corner plugin.
If you are making a small box, make it into a component, make a copy and scale it up, then work on the enlarged copy, so rounding the corners doesn’t try (and fail) to make very small edges.
@DaveR has posted numerous examples on the forum about this.
See also the links to videos in this thread
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Working on a scaled up copy of the component is definitely a good idea in this case.
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Dang it! I just knew if I posted it then it would turn out to be really easy and obvious!
LOL! Yeah AND my segments are much lower than they used to be but divisible by 12! I listen to Mr. Dave! 