(Slightly revised post to avoid being treated as a duplicate.)
I will try to get in touch with the tax people, but doubt that TIAA will allow that.
I would think that in filing form 4852 I could include a note pointing out that all other 1099-Rs issued on this same account were clearly for a Roth. Plus, as you said, the 1099-R for the correction payment is problematic for the IRS because of the contradiction between the “7” code and lack of a check in the line 7 box. I could point that out as well.
Then, if Form 4852 doesn’t work, I could file Form 8606, Part III as an amendment.
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When I said I had not filed Form 8606 in the past , I was referring only to the annuity payments, the only Roth IRA distributions I have ever received. According to the 1040 line 15/4 instructions, I did not need to file the 8606 for that because the 1099-Rs were all coded “Q”. The Roth IRAs originating from the 403(b) starting in 2009 were qualified from the very beginning, because sometime before 2001 I had converted a T-IRA originating from a 401(k) to a Roth. The earliest I could have done this was 1998, when I was 62 years old. I have never taken any distributions from that Roth.
I did file Form 8606 for the Roth IRA conversions in 2009-12, with the following exceptions:
2009 rollover/conversion from 403(b) – I attached an explanation of line 16.
2012 conversion from T-IRA – I can find no copy of Form 8606, but can’t believe I didn’t file it. Perhaps I failed to copy it. I did attach an explanation of line 15.
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So, getting back to filing Form 8606, Part III:
On lines 19 and 21 I would enter the correction payment. I’m not sure whether this should include the estimated earnings on the underpayment, but that’s a small point.
For line 22, I need to fill out the “Basis in Regular Roth IRA Contributions Worksheet”, which is based on “the most recent year prior to 2020 you reported distributions on Form 8606.” I have nothing to enter on this Worksheet, because, as explained above, I have never been required to report the annuity payments on Form 8606. So the result is zero for line 22 of Form 8606, and line 23 is the correction payment.
For line 24, since my 2014-19 annuity payments exceed zero (my basis in regular Roth IRA contributions), I need to refer to the “Basis in Roth IRA Conversions . . . “ chart.
Does the word “contributions” in the heading for column 1 include conversions?
If it does, should I include all of the following?
Roth IRA originating from 401(k)
Roth IRA originating from 403(b) – not used to purchase annuity
Roth IRA originating from 403(b) – used to purchase annuity
However, there’s a glitch in that “the most recent year” is defined in terms of lines 19 and 22 of Form 8606, and I’ve never before had to file a Form 8606 with Part III filled out.