Hi aataxes,
yeah, like you said, that "short sale" is not for options but more for like short stocks...
for example, if you write a call option for strike price $100, and when expire date reach, stock price is $90, then you dont need to "buy" another option to broker/lender to "close" your option,
same for buying a call option and expired with strike price higher than stock price.
reporting of long/short options should refer to IRS pub550, unfortunately , there it only says, if you write a option, acquire date = closing date/expire date, if you buy a option then disposition date = closing date/expire date. But it does not clearly saying when write a option what should you do with deposition date , it suggest write a "expire" as deposition date in case of write a call and the call expires. So in theory, 8949 column C deposition even could dont have a date but just word "expire", and I really think TT should have a better way to allow user ignore deposition date is earlier than aquire date as long as user know these info are auto-imported from 1099b and are matching 1099b.
Bottom line, matching 1099B info is more important and I dont think it is wrong to have sold date earlier than aquire date in case of writing option on 8949, and you can force TT to ignore these warnings by just continue to next step on TT, as long as you are sure all info is matching your 1099B.
