I have experienced a similar failure of TTax of not importing 1 of my 3 2022 1099-Rs to the 2023 return.
All three were properly imported from 2021 to 2022.
I checked in all prior years that the DO NOT TRANSFER box was NOT checked; nor the 2b box for TOTAL DISTRIBUTION.
However, there is a chance that last year I may have tried to populate the form by connecting online with the Investment Co, rather than manually. I just can't remember, but probably was.
So, maybe it is related to how the form was populated and if TTax assumes I'll do it that way again.
