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It does. It is on the same screen as where it asks for the total proceeds.
All the options in the investment section ask for the cost. For the date, if you enter that you are entering multiple transactions then it only asks in the drop down if it is a long term or short term sale.
I did additional research on this question. The entry dates option only appears if you click the 1-3 transactions option. If you click the 4 or more option, the date entry option does not appear, and TurboTax tells you to mail in Form 8453 plus your 1099B report from your broker.
When you have 4+ transactions, TurboTax gives you the option to enter a summary of each section (long term, short term) or each individual transaction one-by-one.
If you choose to enter the summary, you will be prompted to enter the totals and then upload the 1099B.
If you choose to enter the individual transactions, you will be able to provide all the detail from the 1099B, including dates acquired and sold.
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