Yes to both questions (if you're using the Online version of TurboTax):
- To enter stock transactions reported on Form 1099-B you do need to upgrade from TurboTaxDeluxe to Premier.
- You can upgrade at any time, without losing any of the information you've already entered.
To upgrade while in your return, just click Upgrade in the black bar to the left of your screen (just above Tax Tools) and follow the instructions on the screen
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