This thread is assuming that this is an uncovered short sale.
If that is the case, then I agree that an uncovered short sale will always be short term.
This is due to the fact that the holding period is deemed to begin when the stock is purchased to close out the short sale (as noted by @fanfare ).
As a result, you have a one day holding period.
Brokers do not always report these correctly, and as a result, I would imagine that this causes issues within TT if downloaded.
If the OP is dealing with anything other than an uncovered short sale, then it becomes significantly more complicated.
*A reminder that posts in a forum such as this do not constitute tax advice.
Also keep in mind the date of replies, as tax law changes.
