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If TurboTax is providing that message to change the holding period, you might want to double-check the information about the transaction. If this was uploaded, there may have been an error. You can delete that entry and type the 1099-B in yourself.
To enter an investment sale from a brokerage account (1099-B), follow the steps below.
The holding period is determined by the Box category you select for Form 8949.
The dates do not matter.
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