Start by choosing your option type. ISOs (incentive stock options) are reserved for employees and can qualify for long-term capital gains treatment if you meet two holding periods. NSOs (non-qualified stock options) can go to employees, contractors, or directors and are taxed as ordinary income at exercise. The tax math diverges sharply between the two, so this is the most important field.
Enter the number of options, the strike price per share (what you pay to exercise), and the current fair market value (FMV). The gap between FMV and strike is your spread — this is what the IRS considers compensation income for NSOs and an AMT preference item for ISOs. If you plan to sell, enter an estimated sale price; otherwise leave it equal to FMV to model an exercise-and-hold.
Pick a holding period. For ISOs, "long-term qualifying" requires holding shares at least 1 year after exercise AND 2 years from the grant date. Miss either window and the sale becomes a disqualifying disposition, taxed like NSO ordinary income. For NSOs, holding past 1 year only affects the appreciation above FMV (which becomes long-term capital gain instead of short-term).
Enter your other annual income and filing status. The calculator stacks the option income on top of your wages to find the correct marginal bracket. A $100,000 spread on top of a $250,000 salary lands mostly in the 32-35% brackets, not the average 22-24%.
The result card shows your after-tax value, broken down by ordinary income, capital gains, and total tax. If you selected ISO with long-term holding and the spread is meaningful, watch for the AMT alert — it estimates the alternative minimum tax you may owe in April of the exercise year, even if you never sold a single share.