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Best Answer Click here
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You can't annualize for Federal if there are two schedule C's (or couldn't in prior years...).
MY solution was to (in a separate file) annualize and compute the penalty if any. Then force the penalty in the file to be used for efiling. IF/WHEN the government assessed a larger penalty, I'd print out the F 2210 & annualizing worksheets to use to answer the notice.
All with the consent of the client so they weren't surprised when the nasty gram from the government arrived.
YMMV vis a vis Montana
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Welcome to the community and thank you for posting your first question. The diagnostic that you are generating is new this year and is generating because annualization of underpayment of estimated tax does not meet e-file specification for MT and will not be allowed to be efiled.