@ThomasTheSecond This is the part that you're missing - you can't enter the 2021 1099-R on your 2021 return.
The 2021 1099-R is for 2020. You put it on your 2020 return. It's already done. Even though you got it with a 2021 date on it and you have it ready to go you should not enter it on your 2021 return. You already entered it on your 2020 return. It is done.
Now you are going to make a contribution in 2022 for 2021. You are going to enter the amounts that you contribute in 2021 onto your 2021 return because the contribution is for 2021. You do not need a 1099-R for that. Next year you will get a 1099-R for the contribution but you will not enter it onto your 2022 return because it is already on your 2021 return.
This process will continue for as long as you continue to make contributions in the allowed period after the end of the calendar year. This is what the IRS expects you to do.
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