The exercise and the sale are separate. Whether you sell the shares at the time you exercise stock options depends on various factors. At exercise, you can usually...
When restricted stock, restricted stock units, or performance shares vest, whether you sell or hold the shares depends on various factors. Some of them are under your control...
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 stockbroker...
Your company uses one or more "captive" brokerage firms or a transfer agent for...
You will need to activate an account. If you must exercise your stock options with a...
If you have more than one batch of company stock, you are responsible for providing your broker with enough information to identify which shares to sell. If you do not specify...
You can place four types of sell orders, depending on your brokerage firm and company rules...
The default method for the distribution of sales proceeds in a cashless exercise is holding them in an account at the brokerage firm...
While you rarely pay commission for the option exercise or ESPP purchase, you owe it when you...
The commission either reduced the sale proceeds or was reported...
The amount of your capital gain is the difference between your sales price and your tax basis in the stock. However, with stock from equity compensation, your tax basis can be harder to determine. It is...
The treatment for tax-loss harvesting is similar to that of owning and selling any two stocks. The income-tax reporting for multiple transactions is...
Your broker will periodically send you transaction statements...
You recognize ordinary income for the full value of the cash payment. Any deferred portion of the cash sale proceeds is not taxable until...
If you sell company shares for a loss and buy more company shares within 30 calendar days before or after the loss transaction, the federal tax code will...
Form 1099-B or the equivalent substitute statement is necessary for the accurate completion of your tax return. Five facts you must know about this reporting to avoid tax-return mistakes are...
You should almost always receive Form 1099-B. The only exception occurs if certain requirements under IRS Rev. Proc. 2002-50 are met. This revenue procedure allows...
Under the FBAR and FATCA rules, you may have special IRS reporting requirements if you hold assets in a bank outside the US. This FAQ explains the requirements and the severe penalties that the IRS imposes for noncompliance...
Blackout periods are times when some or all of a company's employees are prohibited from trading its securities (sometimes including the exercise of stock options). Window periods are times when trading by those employees is allowed. A company imposes a blackout when it...
To prevent insider trading, and to reduce the need to constantly monitor and evaluate individual requests to trade stock, most companies prohibit employees from trading their stock during certain timeframes. These interludes are known as...
Using a blind trust goes beyond the protections of Rule 10b5-1 plans, yet has more restrictions. These are irrevocable grantor trusts with...
"Garnishment" is a legal process in which a debtor pays an obligation with property and/or goods that are owed to or belong to the debtor but are in the hands of a third party. Whether this remedy applies to stock options depends...
Tax 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.
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