If neither of my boxes are checked in 2b of my 1099-R, then what do I indicate on the return? It won't let me continue

It is common that neither of the boxes in 2b are checked.  It may be something else that is hindering you moving forward.

• Do you have an entry in Box 1?
• Do you have an entry in Box 7?
• Have you completed all of the Payer's information?

In some situations ...with a box TTX is complaining about?

Especially for 1099-R forms that are being re-used this year...if the box is not checked on your paper 1099-R form, sometimes you have to "X" and then un"X" it, just to show you've dealt with it.  Then you can move on.

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