@stephaneich,
I also have TD Ameritrade, and have sold (short) a few options (naked) in 2020, which then expired.
In reading the instructions on the "Proceeds from Broker and Barter Exchange Transactions" section of the TD Ameritrade 1099-B - I see this:
"Long positions are reported based on the trade date and short positions are reported based on the settlement date of the trade."
In TurboTax - I'm going to update all my sold (short) options that needed review as:
Sales Info -> Type: Options (have to manually change this)
Date Acquired (no change) and Date Sold / Disposed of: The expiration date, which TD reported on the form, and is already filled in correctly as the settlement date
Sold or Expired: Sold (I have to select this) - Like others have posted in this thread - cannot chose expired because it zeros out the proceeds/gains. If TT had an option for short vs. long on options - then they could make Sold vs. Expired work correctly - but sold seems to work to match up the gains.
Everything else I'm leaving as imported. So basically I'm only changing the type, and choosing Sold, then moving on. Hope it works, seems to reflect the detail reported on the 1099-B.
Thanks,
Kevin
