Free educational tool · Investing

Stock Option Planning Engine

Identify compensation-income, AMT, holding-period, liquidity, and basis questions before exercise or sale.

Tax year 2026 · Last reviewed 2026-07-29 · Inputs stay in your browser

Investing · Educational Decision Engine

Stock Option Planning Engine

Compare the immediate spread, cash required, and general ISO or nonstatutory option tax signals. This is not an exercise, sale, valuation, or investment recommendation.

Option type shown in plan documentsConfirm the grant agreement and employer records.

Options in this scenarioUse vested and exercisable options only.

Exercise price per shareFrom the grant agreement.

Fair market value per share at exercisePrivate-company valuation requires appropriate company support.

Scenario sale price per shareA scenario only—not a valuation or forecast.

Actual grant date, if knownWhen all three dates are entered, actual dates control instead of rounded year inputs.

Actual exercise date, if knownUse the legal exercise date shown in company records.

Actual sale date, if knownISO anniversary tests require a sale more than two years after grant and more than one year after exercise.

Years from grant to saleISO qualifying disposition generally requires more than two years after grant.

Years from exercise to saleISO qualifying disposition generally requires more than one year after exercise.

Exercise and sale occur togetherA cashless transaction changes liquidity and holding-period analysis.Shares are private or illiquidTax may be due before liquidity exists.Services were performed in multiple states or countriesCompensation sourcing may require allocation.

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Stock Option Planning Engine

Stock Option Planning Engine

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Use this result to prepare for professional review—not to take a filing or transaction position.