How are stock options reported on Form 1099-B?

Determine from which account you are missing your consolidated form 1099. If you are missing a consolidated form 1099, please verify that you received interest (including interest on free cash), dividend or payment in lieu, or you sold shares of stock, you bought or sold futures contracts. For the dates when the tax forms will be made available, please see: …

Assets held for investment purposes, including as stocks, options and bonds, are classified by the IRS as capital assets. When such assets are sold, a capital gain or loss is realized on the sale. If the capital asset is sold for a price greater than its purchase price, then a capital gain has been realized; if less, then a capital loss has been realized. In determining whether a capital gain or loss has been realized, adjustments to the purchase and sales price may be allowed to recognize certain transaction costs such as commissions and other specific adjustments…

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…

A Long stock position has to be held more than a one year period before a closing trade would be considered a Long Term profit gain or loss.  If you sold a long stock position that you owned for less than one year it would be considered a Short Term gain or loss.  Any Short stock position you hold is borrowed therefore it is always considered to be a Short Term Gain or Loss regardless of when it was opened and then closed…