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Caulk will hide a multitude of sins but 3/8" is a lot to hide. Your crown has enough of a top edge that I would recommend scribing most of the difference and the caulking the rest. Remember that you also have to deal with the problem once you get around the corner.
 

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Caulk will hide a multitude of sins but 3/8" is a lot to hide. Your crown has enough of a top edge that I would recommend scribing most of the difference and the caulking the rest. Remember that you also have to deal with the problem once you get around the corner.
It is a huge gap, but there isn't much choice in a case like this. I had to deal with this in my house. I tried altering the miter in order to flex it upwards, but that changes the profile and creates a lot of flex .

If I ever had to run crown again and knew I had a wavy ceiling, I would start with a flat moulding against the ceiling, shim and caulk as needed, then there is a nice flat surface to butt the crown against.

But yes 3/8" is not a huge gap to fill, you probably could do it without backer rod. You can use caulk, nail filler or even drywall compound. The key is let it shrink for a couple days, then come back with caulk and a putty knife, not your finger!

But, like finishing furniture, what do I know? I know I don't look at the ceiling much, until the LOML asks me why I'm driving 8 hours to buy lumber .............:LOL:
 
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