In my 403b, I did an in-plan Roth conversion early in the year, and I did a pre-tax rollover into a Roth later in the year (plan does not allow more than 1 in-plan conversion each calendar year). The 1099R that I received showed both amounts together and all of it as taxable, which is what I expected. When entering into TurboTax, the only options I have are that the entire amount was converted (in-plan) or that the entire amount was rolled into a Roth IRA. It only affects how things are filled in section "B" on the 1099 R entry form (when I look at forms view). The end result is that the taxes are the same. However, I don't like that TT will not let me truthfully answer the interview question. TT is assuming that each 1099R corresponds to a single transaction, and maybe it doesn't matter, but it took me a little while to figure out that it doesn't make a difference. I'm using TT to reduce confusion, not increase it.
