The 1099-B uses terminology like " Long-Term sales reported to the IRS with Box B checked ." Long-Term means you held it more than a year. Short-Term means you held it one year or less. (You can calculate both these from the dates purchased and sold .)
Can I report a long-term gain or loss on a 1099-B?
Apply the rule in section 1233 (d), if applicable. Except as provided below, in addition to checking the applicable short-term or long-term box, you are required to check the “Ordinary” checkbox if all or a portion of the gain or loss may be ordinary. You may not report both short-term and long-term gain or loss on the same Form 1099-B.
Can a broker report a long-term loss on a 1099-B?
You may not report both short-term and long-term gain or loss on the same Form 1099-B. For transactions that are denominated in a currency other than the U.S. dollar, brokers must check the "Ordinary" checkbox because these transactions may be section 988 transactions to the customer.
