So when a stock was trading at about $15 a share in Nov 2019, i sold a put option on it for strike $8 that expired January 2021. Isn't that a long term gain?

[paul-j-heckman]

turbotax seems to be importing it from Interactive Brokers as "acquired date" on the expiration date, and "sold" date also on the expiration date.  But I didn't take any action upon it (it just expired), and I had acquired it over a year earlier.  shouldn't this get long term tax treatment?

[Mike9241]

short sales only get short-term treatment except possibly in certain hedging transactions.  so your sale in 2019 with expiration in 2021 is short-term.   

[fanfare]

Your broker report is correct.

In order to close a short you must go to the market and acquire some securities.

The acquired date is the date you closed the short sale.
For Stocks, the disposed date is two business days later (settlement).
Options settle in one day.

If you did not have a loss, the disposed date is the same as the acquired date.

Note to those for whom it is not obvious: Date Acquired and Date Disposed refer to Columns (b) and (c) on Form 8949 that you will report to the IRS.
Your trade date is the date you closed the position and goes in (b). Settlement date must be calculated taking into account weekends and market holidays.
From this you can see that a short is always a short term capital gain or loss, no matter how long you are short.

Option write, expires:
Since you are short, the Date Acquired shows the date of expiration,
Enter "Expired" in 8949 column e) cost, but Turbo Tax won't let you do that directly so
you have to go through the "Add More Details" screen and select "Expired". Last I tried, this had no effect either.

[fanfare]

Don't be like Jerome Powell and start every statement with "So".