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I did talk to TIAA, and they also sent a letter.  They aren't sending a 1099 in the year it reached maturity (2021), and there is no gain, or loss.  But TIAA provided 1099s that indicated OID gains every year prior (2016-2020), and these gains were not sent to me ever.  I need to take a loss on my tax form to offset the reported gains I was taxed on in prior years because TIAA never paid any gain.

 

BTW, this is a CD, not a bond. 

 

So are you saying that these should reported as a capital loss on Sched D?  I tried putting a negative value in Sched B, and TurboTax would not allow it.