Do gross proceeds on Form 1099-B include sale transactions that occurred in December but settled in January?

Yes. Proceeds related to short sales of securities are reported on a trade-date basis in the current year the trade is executed and not the year the sale is covered. Short sales of options are not reported. Rules that apply to short sales are complex. Refer to…

Form 1099 reporting may result in a disparity between what appears on your monthly and yearly activity statements and what is reported on your Form 1099. For example, transactions reported on Form 1099 must be reported on the trade date. Your activity statements may reflect transactions based on the settlement date. In addition, unlike dividends from individual securities which are taxed in the year dividends are paid, mutual fund distributions declared as payable to shareholders of record in October, November or December and paid in January of the following year are taxable to shareholders based on the record date, and not the payment date. Mutual fund distributions with a December record date and paid in January 2, are reported and taxed as dividend distributions in the year they were declared…

In the case of a closing stock sale for U.S. taxpayers, the reporting date for Form 1099-B purposes is the trade date. Accordingly, a closing securities trade executed on the last date of the year will be reported on that year’s tax reporting despite the fact that it will settle in the following year…

As proceeds are reported on a trade date basis a sale is reportable in the year it is executed not settled. In the case of bond sales which take place in December but which do not settle until the following year, the sale proceeds will be reported in the year of the trade, and accrued interest, if any, will be reported included in the following year’s 1099-INT, when the funds are received in your account…