Recover Signature Block Stock Plan For Free

Purchase shares: Typically at the end of the purchase period (i.e. purchase date), you officially purchase the shares. Sell shares: You can sell your ESPP shares right after you purchase them or hold onto them.

Your ESPP is taxed when you sell shares. You have taxable ordinary income to report as well as any capital gain/loss from the sale. As you file your taxes, you'll want to consider if you made a qualifying or disqualifying disposition.

With employee stock purchase plans (ESPP), when you leave, you'll no longer be able to buy shares in the plan. Depending on the plan, withholding may occur for months before the next pre-determined purchase window.

If your ESPP stock is sold more than 12 months after the purchase date, any appreciation beyond the discount will be taxed as a long-term capital gain. Long-term capital gain tax rates are typically much lower than ordinary income tax rates, ranging from 0% to 20% federal, depending on your income.

You sold the stock at least two years after the offering (grant date) and at least one year after the exercise (purchase date). If so, a portion of the profit (the ?bargain element?) is considered compensation income (taxed at regular rates) on your Form 1040.

To get a favorable tax treatment, you have to hold the shares purchased under a Section 423 plan at least one year after the purchase date, and two years after the grant date. Q.

The bottom line on ESPPs If you can afford it, you should participate up to the full amount and then sell the shares as soon as you can. You might even consider prioritizing your ESPP over 401(k) contributions, depending on your specific financial situation, because your after-tax returns could be higher.