I am a Federal retiree, but not as a former law enforcement member. I had the same problem, but noted the amount in Box 5 of the 1099-R did not carry over to the worksheets for the 1099's or for medical expenses. one of the the "more info" notes that I clicked on when completing one of the pages indicated the amount in box 5 would carry over to the total health insurance amount. Box 5 on my 1099-R says the number can represent more than just insurance premiums, but, in my case, the number was exactly the amount of my premiums. Is it possible the TurboTax program needs to ask what that number represents or, perhaps, I just missed where it does so?
