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Yes. The box will actually have an x.
Yes, in this case the "X" would be a check in our system, depending on who provided the form it could be a check or "X". You may be referring to Box 2b, Taxable amount not determined box, and total distribution box. When you select it TurboTax enters a checkmark indicating there's a mark on your 1099R form for that box. Another one they ask about is if IRA/SEP/SIMPLE is checked or has an "X".

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