There is not such thing as a "403B with some designated Roth contributions under it". A 403(b) Roth (Designated Roth) is a separate account from a 403(b). They are two types of 403 accounts.
A regular 403(b) can contain after-tax money, but that is not a Roth, it is simply after-tax money within the 403(b). When converted to an IRA both the before tax after-tax money can be rolled into a Traditional IRA, or the before-tax can be rolled to a Traditional IRA and the after-tax to a Roth IRA.
However, any after-tax money must be identified in box 5, otherwise it would all be before-tax money that cannot be rolled to a Roth IRA.
And no, you do not need two 1099-0R's from the plan administrator. You need a single 1099-R that identifies that portion of box 1 went to the Traditional IRA and the portion that went to the Roth IRA - the box 5 does that. The 1099-R that you have says that it is all before-tax money and all went to a Traditional IRA.
(It is TurboTax that requires that *you* enter this as two 1099-R's because two destinations are involved and TurboTax is not capable if doing that with one 1099-R, but the box 5 amount must be resolved first).
**Disclaimer: This post is for discussion purposes only and is NOT tax advice. The author takes no responsibility for the accuracy of any information in this post.**
