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With NSOs, you pay ordinary income taxes when you exercise the options, and capital gains taxes when you sell the shares. With ISOs, you only pay taxes when you sell the shares, either ordinary income or capital gains, depending on how long you held the shares first.
ESPP lookback allows you to buy shares at a lower price point. An ESPP lookback allows you to purchase the share price of either A: the enrollment date (1 Jan) or B: the purchase date (30 Jun), whichever is lower.
You report this amount as compensation income on your 2023 Form 1040. You show the sale of the stock on your 2023 Schedule D. It's considered long-term because more than one year passed from the date acquired (January 2, 2022) to the date of sale (January 20, 2023).
In general, you will be taxed on any stock you purchase through an ESPP during the year you sell it. It can be counted either as taxable income or as a deductible loss. The difference between what you paid for the stock and what you received when you sell it is considered a capital gain or loss.
Qualifying disposition: 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.
Form W-2 (or 1099-NEC if you are a nonemployee) Your W-2 (or 1099-NEC) includes the taxable income from your ESPP and, on the W-2, the taxes that have been withheld. This form is provided by your employer. Form 1099-B This IRS form has details about your stock sale and helps you calculate any capital gain/loss.
In an ESPP with a reset feature, the look-back purchase price will "reset" if the stock price at a future purchase date is lower than the stock price on the first day of the offering period. On the date that a reset feature is triggered, the terms of the award have been modified.
Form W-2. Any compensation income received from your employer in the current year is included on Form W-2 in Box 1. If you sold any stock units to cover taxes, this information is included on Form W-2 as well. Review Boxes 12 and 14 as they list any income on Form W-2 related to your employee stock options.