[MrDem]

We are speaking taxwise and they are consider "sold" at a price of $0.00 if they expire worthless.

From the IRS Publication 550:

Option not exercised. If you have a loss because you did not exercise an option to buy or sell, you are considered to have sold or traded the option on the date it expired.

[CharlesWayneCT]

Pretty much the same rule if you have stock and a company goes bankrupt.

“Considered to have” is not the same as “did”.