Has the requirement changed for importing a 1099-B? In 2019 I was able to file using TT Deluxe, but in 2020 it is requiring me to upgrade to TT Premier.

Yes. Form 1099-B is included in TurboTax Premier, TurboTax Live Premier, Self-Employed, and TurboTax Live Self-Employed (online) and in all personal CD/Download versions of TurboTax.

Form 1099-B (Proceeds from Broker and Barter Exchange Transactions) reports the sale of stocks, bonds, mutual funds, and other securities.

Here's where you enter or import your 1099-B in TurboTax:

1. Open (continue) your return if it isn't already open.
2. In TurboTax, search for 1099-B and then select the Jump to link in the search results.
3. Answer Yes to Did you sell stocks, mutual funds, bonds, or other investments in 2020?
   • If you see Here's the info we have for these investment sales, select Add More Sales.
4. Answer Yes to Did you get a 1099-B or brokerage statement for these sales?
5. At Let's get your tax info, choose how you want to enter your 1099-B (import or type it in yourself).
6. Follow the instructions.