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Basics: Sales




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How do I sell shares that I acquire through a stock option exercise, restricted stock vesting, or ESPP?
Whether you hold stock certificates, hold your shares in a brokerage account, or have an online trading account, you will need the assistance of a securities firm or a stockbroker to sell your stock. Your company will probably require your shares to be deposited in an account at a specific securities firm or transfer agent. The brokerage firm you use can help you with its procedures, which may allow online and telephone sales.

If you want to sell specific shares (e.g., highest- or lowest-cost shares) according to when you purchased them and at what price, you need to specifically identify them in some way through your brokerage firm's system and receive a confirmation of this. Otherwise, the first shares purchased are considered the first ones sold for calculating your gain or loss on the sale. For details about the tax reporting of the sales, including annotated examples of Schedule D, see the relevant section of the Tax Center.

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Annotated diagram of Schedule DTax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.