if you are an investor or a trader that has not made the 475(f) election

if you buy and it expires or you buy and then sell report as a capital gain on form 8949 (1099-B worksheet) in the year in which it expires or sold

in either case, report Long-term or Short-term based on the period held.

if you sell short and it expires or you sell short and buy the reporting is the same as above except the gain or loss will always be Short-term.

the wash sale rules apply to stock options unless you are a trader and made the 475(f) election. if you have, then you treat the gains and losses as ordinary gains and losses (except for those held for investment) that are reported on Part II of Form 4797, Sales of Business Property. Neither the limitations on capital losses nor the wash sale rules apply to traders using the mark-to-market method {475(f)} of accounting.  at year-end, the market value of open positions is determined and gain or loss is reported for that year based on the difference between market value and proceeds or cost of the options.

If you enter into a closing transaction by paying an amount equal to the value of the put or call at the time of the payment, the difference between the amount you pay and the amount you receive for the put or call is a short-term capital gain or loss.

In order to close a short you must go to the market and acquire some securities, in this case, some options.

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.

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.

If an option that was granted (written) expired, enter the expiration date in column (b) and

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.

I add "Expired" in the description.

From this you can see that a short is always a short term capital gain or loss, no matter how long you are short.

Schwab reports this correctly on your 1099-B.

Some other brokers in the past did not, and still may not, but I suppose this is changing over time as they get "educated" by the IRS.

In any case, your option trades are covered transactions.

Covered transactions without adjustments do not require Form 8949.