For a short option, think in terms of opening and closing the position. If you sell a put in XYZ and your proceeds are $100 and it expires worthless, enter the transaction with a $0.00 cost basis, and proceeds of $100. If you bought to cover (closed the position), that is your cost basis. The date you opened the position (sold the put) is your acquisition date. The date the put expired, or the date you bought to cover is the date sold,
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