I, too, had what sounds like the same problem you and a few others have had: Distributions from a traditional IRA to which we have made non-deductible contributions in the past, but no contributions in the past few years since we retired (and none in 2021), and for which we have been filing Forms 8606 each year since we made the non-deductible contributions. No problems in past years when we have been filing our taxes, but this year TurboTax did not prompt for the 2021 year-end fair market value or basis for prior year. I, too, spent several hours on the phone with two different support people trying everything we can think of to force TurboTax to ask for these two pieces of information, but with no luck.
In prowling around through this Community forum some more, though, I found another recent entry (March 2022) by a user named "MNOP" who sounded like he was having the same problem and noticed his following statement: "I spent nearly 5 hours on the phone with a "tax expert" (Sat, 5Mar) (today 10 Mar). The end result seemed to be I had to wait for an update scheduled for 31 Mar."
Since for me it was now March 31, 2022, I decided to give TurboTax one more try. I deleted all of the "Wages" information (1099-INTs, 1099-Rs, 1099-DIVs, etc) and re-entered it. This time TurboTax did prompt me for the fair market value and basis and the associated Form 8606 now looks reasonable. (I still need to check the entire return before I'll pronounce it "correct.")
Was there truly a software update on March 31? Or did I just happen to clear something else out that was causing the problem when I deleted all of the "Wages" information? I guess we'll never know.
