A broker or barter exchange must file Form 1099-B, Proceeds From Broker and Barter Exchange Transactions, for each person:
For whom the broker has sold (including short sales) stocks, commodities, regulated futures contracts, foreign currency contracts (pursuant to a forward contract or regulated futures contract), forward contracts, debt instruments, options, securities futures contracts, etc., for cash;
Who received cash, stock, or other property from a corporation that the broker knows or has reason to know has had its stock acquired in an acquisition of control or had a substantial change in capital structure reportable on Form 8806; or
Who exchanged property or services through a barter exchange.
How many transactions to report on each form. Report each transaction (other than regulated futures, foreign currency, or Section 1256 option contracts) on a separate Form 1099-B. Report transactions involving regulated futures, foreign currency, or Section 1256 option contracts on an aggregate basis. However, you may report these contracts on an aggregate basis on a separate Form 1099-B for each type of contract.
How many forms to file for each transaction. Report sales of each of the following types of securities on a separate Form 1099-B, even if all three types were sold in a single transaction.
Covered securities (defined later) with short-term gain or loss.
Covered securities with long-term gain or loss.
Noncovered securities (securities that are not covered securities) if you choose to check box 5 when reporting their sale.
Substitute statements. Brokers that use substitute statements may be able to report customer transactions (stock sales (Form 1099-B), interest earned (Forms 1099-INT and OID), dividends (Form 1099-DIV), and foreign taxes paid (Form 1099-INT)) for the year on a single substitute statement. For details, see Pub. 1179, General Rules and Specifications for Substitute Forms 1096, 1098, 1099, 5498, and Certain Other Information Returns, which provides the rules for substitute forms.