When to exercise stock options: US guide
Have a look at a practical guide to when to exercise stock options: tax trade‑offs, timelines, and liquidity events to help you choose the best moment today.
If your employer offers stock options as part of your compensation, you've probably wondered how they are taxed and what that means for your wallet. The tax rules can feel confusing, especially when you're trying to figure out if you owe taxes now, later, or both.
In short, you might pay taxes when you exercise your options, when you sell your shares, or at both points, depending on the type of options you have.
Here's everything you need to know.
We'll also introduce Wise — your international money transfer alternative. Use Wise to send stress-free transfers to over 140 countries - all at the standard mid-market exchange rate.
| Table of contents |
|---|
Stock options let you buy company shares at a locked-in price, called the strike price or exercise price. Your employer grants you these options, but you don't own the shares yet.
For example, maybe your company grants you options with a strike price of 10 USD per share. If the company's stock value grows to 30 USD per share, you can still buy shares at 10 USD each and get a profit of 20 USD per share.
You typically need to wait through a vesting period before you can exercise your options. Once vested, you can choose to exercise them by paying the strike price to purchase the shares. After that, you own the stock and can hold it or sell it.
Different stock options are taxed differently, depending on whether you hold incentive stock options (ISOs) or non-qualified stock options (NSOs).
Let's take a closer look at how it works:
Stock options come in two types:
- Incentive stock options (ISOs) can help you pay less tax if you follow certain rules
- Non-qualified stock options (NSOs) are taxed like regular income when you buy the shares
ISOs are only available to employees and have lower taxes if you follow the appropriate IRS rules. When you exercise ISOs, you generally don't owe regular income tax right away. However, you may trigger something called the alternative minimum tax.
If you hold ISOs long enough after exercising, any profit when you sell can be taxed at the lower capital gains rate instead of your regular income rate.
NSOs are for employees, contractors, and advisors.
When you exercise NSOs, you'll pay regular income tax on the gap between what you paid and what the shares are worth at that time. Your employer will typically withhold taxes at this point, similar to how they withhold from your regular paycheck.
Stock options create potential tax obligations at two important moments: exercise and sale.
When you exercise your options, you're buying the shares. For NSOs, this triggers ordinary income tax on any gain right away. For ISOs, you may avoid regular income tax at this point, but the gain could affect your alternative minimum tax calculation.
When you sell your shares, any profit from the sale is subject to capital gains tax. The amount depends on how long you held the shares and whether you met the requirements for ISOs.
If you sell within 1 year of exercising, you'll pay short-term capital gains tax at your regular income rate. If you hold the shares for more than 1 year, you'll pay long-term capital gains tax, which is lower for most people.¹
| 💡 Learn how RSUs are taxed. |
|---|
Wise can help you get a better deal on currency conversion in over 40 currencies, with the mid-market exchange rate and low fees from 0.41%*.
Open a free personal Wise account online or in the Wise app, and order a linked multi-currency card for spending and withdrawals in 145+ countries.
There’s no fee to spend any currency you hold, and no foreign transaction fee to worry about.
Use your account when you travel or shop online in foreign currencies, send payments to 40+ currencies, and get your own local account details to get paid from 145+ countries.
Say goodbye to overcomplicated currency exchange.
*Please see Terms of Use for your region or visit Wise Fees & Pricing for the most up to date pricing and fee information
This is the same tax you pay on your regular salary.
When you exercise NSOs, the IRS treats the difference between your strike price and the current market value as ordinary income. Your tax rate depends on your total income and tax bracket. It can range from 10% to 37% for federal taxes.²
Your employer will withhold this tax when you exercise, similar to how they withhold taxes from your paycheck. You'll also owe payroll taxes like Social Security and Medicare on this amount.
Capital gains tax applies when you sell your shares for more than you paid for them. The rate you pay depends on how long you held the shares after exercising:¹
Long-term capital gains rates are lower than ordinary income rates for most people, which is why holding shares longer can reduce your tax bill.
The AMT is a parallel tax system that applies only to ISOs.
When you exercise ISOs, the difference between your strike price and the current market value gets added to your AMT calculation, even though you don't pay regular income tax on it.
The IRS calculates both your regular tax and your AMT, and you pay whichever amount is higher. This can create a surprise tax bill if you exercise ISOs when the stock value has grown a lot.
Keep in mind that the AMT only applies if you exercise ISOs and don't sell them in the same tax year.
Your employer and brokerage will send you tax forms that report your stock option activity to the IRS.
You'll need these forms to file your taxes:
- Form 3921 reports ISO exercises and includes details like the grant date, exercise date, strike price, and the market value when you exercised
- Form W-2 includes the ordinary income from NSO exercises, along with your regular salary, and shows how much tax your employer withheld
- Form 1099-B reports stock sales and shows the proceeds from selling your shares, which you'll use to calculate capital gains or losses
You'll use the information on these forms to calculate your cost basis and report any gains or losses when you sell your shares.
| 💡 Learn more about how to report RSUs on your tax return. |
|---|
It depends on a few different things.
For NSOs, you'll pay ordinary income tax when you exercise at rates between 10% and 37% at the federal level, plus state taxes in states that have income tax.2
For ISOs, you may not owe regular income tax when you exercise, but you could trigger AMT. When you sell, you'll pay capital gains tax on any profit.
You pay taxes at two different times, but not on the same income twice.
For NSOs, you pay regular income tax on the gain when you buy the shares. If you later sell them at a higher price, you only pay capital gains tax on the extra profit above what they were worth when you exercised.
For ISOs, if you meet the holding requirements, you may only pay capital gains tax when you sell. If you don't meet the requirements, you'll pay ordinary income tax on part of the gain and capital gains tax on any additional profit from the sale.
The main difference is when and how much tax you pay.
NSOs are simpler but typically result in higher taxes. You pay ordinary income tax immediately when you exercise, and your employer withholds the tax. Any profit when you sell is taxed as capital gains. ISOs can mean lower taxes, but there are IRS rules that you'll need to follow.
Stock option taxation is complicated, but the process becomes a lot clearer once you break it down.
You're taxed when you exercise your options and again on any profit when you sell your shares. The type of options you have and how long you hold them ultimately determines how much tax you'll owe.
Do you want to transfer your stock option proceeds to another country? Banks and money transfer services often charge high fees and top them off with currency exchange rate markups.
You can lose a lot of money on this.
For a smarter and more transparent alternative, try Wise.
With Wise, you can send secure and trackable large amount transfers to 140+ countries worldwide with transparent fees and the fair mid-market exchange rate.
Have a look at the main benefits for using Wise to send large transfers:
Sources
Sources checked 05/27/2026
*Please see terms of use and product availability for your region or visit Wise fees and pricing for the most up to date pricing and fee information.
This publication is provided for general information purposes and does not constitute legal, tax or other professional advice from Wise Payments Limited or its subsidiaries and its affiliates, and it is not intended as a substitute for obtaining advice from a financial advisor or any other professional.
We make no representations, warranties or guarantees, whether expressed or implied, that the content in the publication is accurate, complete or up to date.
Have a look at a practical guide to when to exercise stock options: tax trade‑offs, timelines, and liquidity events to help you choose the best moment today.
Understand how equity vesting works for Americans: common schedules, cliffs, taxes, and what happens when you leave – so you can plan and decide confidently.
How does stock option vesting work in the US? Learn vesting schedules, cliffs, taxes, and what happens when you leave a job or change roles.
Read on for a step-by-step guide to selling inherited property abroad, including fees, taxes, and timelines.
Thinking of moving to Spain or Portugal? Find out what tax programs they have for expats to decide which might be better for you.
Need to report the sale of an inherited property abroad? Read on to learn how to avoid capital gains tax and other tips.