I disagree with dmertz's answer.
I believe the answer is Yes.
Recently many companies (and the broker such as fidelity managing the 401K) have have started to offer AFTER_TAX contributions to the 401K which as converted each time the contribution is made as "in-plan conversion" to the roth of same plan. IF you for example contributed say 20K pre-tax and your employer contributed 2K as a match then you can contribute up to total of 66K. So in my example you can contribute 66-22=44K of AFTER_TAX - this amount is rolled over to the roth on each and every contribution before the money has chance to earn any income.
So the answer to first question that turbo tax asks is Yes (I agree with what dmertz said) but i believe the answer to the 2nd question is also yes. If it is tradition rollover then the answer is NO (since the original money is after-tax) while for this new kinds of in-plan conversion the answer is YES. I am 90% sure but not 100%. It would be good if turbo tax has a help button on this part of app to help folks differentiate and answer correctly.
