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Work through three separate questions: which shares are vested, when the contract says the option expires after termination, and whether exercising creates a tax bill before you can sell the shares. U.S. federal tax rules also differ for incentive stock options (ISOs) and nonstatutory stock options (NSOs). Your plan and grant agreement control the contractual right; federal law controls tax treatment.
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What happens to your options when employment ends
Unvested options are usually forfeited
Most plain-vanilla plans cancel the portion that has not vested when you leave. The SEC describes this pattern in Staff Accounting Bulletin No. 107: an employee forfeits unvested awards at termination, while vested options may continue for a limited post-termination period. Read the vesting schedule and the termination provisions in your own award agreement rather than assuming any particular result. SEC Staff Accounting Bulletin No. 107
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Vested options can still expire
Vesting gives you the right to exercise a specified number of shares; it does not keep that right open indefinitely. The plan may provide a post-termination exercise window, followed by the option’s expiration. The relevant date can depend on how the plan defines termination, such as your last day of active employment rather than the date your final paycheck arrives. Confirm the official termination date with the plan administrator and obtain the expiry date in writing.
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Is the post-employment window always 90 days?
No. “90 days” is not a universal contractual rule. The SEC’s accounting example says post-termination exercise periods are “typically 30-90 days,” but that is a qualified example, not a survey and not a legal requirement. Your agreement might use a different period, special treatment for retirement or death, or separate rules for misconduct and disability.
The 90-day idea also comes from the federal ISO employment test. Under 26 U.S.C. § 422, an ISO generally must be exercised no later than three months after employment ends to retain statutory ISO treatment; the specified disability exception uses a one-year period. This tax qualification does not extend a contract that expires sooner, and exercising after the applicable period does not revive the option or guarantee ISO treatment.
Find out whether you hold ISOs or NSOs
The grant notice, option agreement, cap-table portal and plan document should identify the option type. The IRS calls an option granted under an incentive stock-option plan a statutory option. Options outside that statutory framework are generally nonstatutory. The distinction affects when income is recognized and what happens if you sell.
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| Issue | ISO | NSO |
|---|---|---|
| Regular income at exercise | Generally none at exercise, although the spread may be an alternative minimum tax (AMT) adjustment when the shares become transferable or are no longer subject to a substantial risk of forfeiture. | For most NSOs without a readily determinable fair market value at grant, the fair market value of the shares at exercise minus the amount paid is compensation income. |
| Employment timing | The federal employment-period test can affect whether the exercise receives statutory treatment; generally, exercise must occur within three months after termination, or within one year in the specified disability case. | No ISO employment-period test applies, but the contractual post-termination deadline still controls. |
| Records to retain | Grant date, exercise date, shares transferred, strike price, fair market value, AMT calculations and later sale records. | Grant and exercise records, compensation reported, withholding information and basis used on a later sale. |
| Sale treatment | Favorable statutory treatment generally requires holding the shares through the later of one year after transfer and two years after grant. An earlier sale can be a disqualifying disposition. | Sale treatment depends on the basis established after exercise and the holding period; the special ISO holding-period test does not apply. |
The IRS summarizes the NSO issue this way: “Most nonstatutory options don’t have a readily determinable fair market value.” IRS Topic no. 427, Stock options
Documents and numbers to collect before deciding
Do not make the decision from a compensation summary alone. Assemble the documents and dates that determine both your legal right and the financial exposure.
- Termination date: Ask which date the plan uses and whether a leave, severance period or change in status alters it.
- Vested share count: Separate vested shares from unvested shares as of that date. Confirm whether vesting accelerates under any change-in-control or other provision that applies to your departure.
- Contractual expiry: Obtain the last day and time you may exercise, the time zone, the payment method and any administrative processing cutoff.
- Option classification: Record whether each grant is an ISO or NSO; a person can hold both.
- Strike price: Calculate the exercise cost as strike price multiplied by the number of shares exercised, then add any required taxes, fees or withholding.
- Current share value and sale path: For a private company, ask whether there is a tender offer, approved secondary transfer or other liquidity event. An internal valuation is not a promise that you can sell at that price.
- Tax records: Preserve grant notices, exercise confirmations, Forms 3921 or 3922 when issued, employer wage reporting and any valuation used for the exercise.
How to evaluate an exercise before the deadline
1. Separate the exercise from the investment
Exercising converts an option into shares. It requires cash for the strike price and may create tax before there is a market in which to sell. After exercise, you own shares whose value can rise, fall or remain illiquid. Federal sources explain tax mechanics; they do not establish a private company’s current value, liquidity or future prospects.
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2. Estimate the tax at exercise
For an NSO, the usual federal calculation is the fair market value on exercise minus the strike price, multiplied by the shares exercised. That spread is compensation income for most NSOs lacking a readily determinable grant-date value. Ask how the employer will report and collect any required withholding.
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3. Test your ability to hold the shares
Ask how long you could keep the shares if no sale window opens. Include the possibility of additional tax, a future capital call, concentration in one company and a total loss. An exercise is not a guaranteed return merely because the current valuation exceeds the strike price.
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4. Compare the available actions
| Action | What it accomplishes | Main exposure to examine |
|---|---|---|
| Exercise all vested options | Converts the full vested amount into shares before the contractual deadline. | Maximum cash requirement, tax exposure and concentration; shares may be illiquid. |
| Exercise only part | Preserves some potential upside while limiting cash and tax exposure. | The unexercised portion can still expire; partial exercises may have separate tax lots and paperwork. |
| Wait within the window | Keeps cash available and allows more information about valuation or liquidity. | The option can expire, and a later share value can increase the tax cost or reduce the economic benefit. |
| Do not exercise | Avoids paying for shares that may never be liquid. | You give up the option’s potential value when it expires. |
These are decision categories, not individualized recommendations. Use the strike price, deadline, tax estimate, liquidity prospects and intended holding period together rather than relying on a single valuation or a 90-day rule of thumb.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.ISO holding periods and what happens when you sell
For favorable statutory treatment, an ISO share generally must be held until the later of one year after the shares are transferred to you and two years after the option was granted. Selling before both periods end is a disqualifying disposition. The sale can produce ordinary income up to the relevant exercise spread; any remaining gain may be capital gain, subject to the facts and current IRS instructions. IRS Publication 525 (2025)
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Reporting a later sale and checking basis
When shares are sold, compare the broker’s Form 1099-B with your exercise and wage records. The IRS cautions that, for options granted on or after January 1, 2014, Form 1099-B may omit compensation that was previously included in basis. You may need an adjustment on Form 8949 so the same income is not taxed twice. The taxpayer remains responsible for the appropriate basis adjustment and for retaining the supporting records. IRS Publication 525 (2025)
Keep a lot-by-lot file containing the grant date, number of shares, exercise date, strike price, fair market value used, compensation included, AMT basis, sale date, proceeds and transaction costs. Do not assume a broker’s reported basis captures the ISO adjustment or the NSO compensation element.
Common mistakes after leaving
- Assuming every option lasts 90 days: Read the agreement and get the actual date from the administrator.
- Counting unvested options: Remove forfeited shares from your calculation unless the documents provide acceleration.
- Confusing grant value with sale value: A private-company valuation does not create a buyer or guarantee proceeds.
- Ignoring tax before liquidity: Exercise cash, NSO compensation tax and possible ISO AMT can arrive before any sale.
- Mixing ISO and NSO lots: Track each grant separately; the tax rules and holding periods differ.
- Using the wrong termination date: A payroll or severance date may not be the plan’s definition of termination.
- Failing to reconcile basis: Review Form 1099-B against Forms 3921, exercise confirmations and employer reporting.
- Waiting until the last day: Payment processing, identity checks, wire cutoffs or company approval can make an apparent deadline earlier in practice.
A practical departure checklist
- Download the current plan, every grant agreement and the latest cap-table statement.
- Ask the administrator to confirm your termination date, vested shares, option type and contractual expiry in writing.
- Calculate the total strike price for any proposed exercise and identify the required payment and withholding method.
- Obtain the current fair-market-value information used for tax reporting and ask how an NSO spread or ISO AMT adjustment will be reported.
- Determine whether you can sell the resulting shares and how long you could hold them without liquidity.
- For ISO grants, put the two-year-from-grant and one-year-from-transfer dates on your calendar.
- Keep all confirmations and reconcile future Forms 1099-B and Form 8949 reporting.
- Have a tax professional review state, local or non-U.S. consequences if those jurisdictions apply; the federal rules do not answer them.
What these rules do not determine
This explanation covers U.S. federal concepts. It does not determine your state’s or locality’s tax, the treatment in another country, whether your employer’s plan permits exercise after your specific departure, the fair value of private shares or your personal tax liability. Those answers require the governing documents, issuer information and your individual facts. Verify the instructions for the tax year in which you exercise or sell.
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