What happens when you exercise an NSO
A Non-Qualified Stock Option gives you the right to buy company stock at a fixed strike price. Nothing is taxed when the option is granted or as it vests. The taxable event is exercise: the moment you buy the shares, the difference between their fair market value and your strike — the bargain element — is treated as ordinary income. It is added to your W-2 and taxed exactly like salary, including Social Security and Medicare.
The 22% withholding gap
Your employer typically withholds federal tax on the bargain element at the 22% supplemental rate. If your real marginal rate is higher, that withholding falls short and the gap lands on you at filing. On a large exercise this can be a five-figure surprise in April. Plan for it by adjusting your withholding or making an estimated payment in the quarter you exercise.
The cost-basis trap
Here is the mistake that quietly costs option holders the most. When you exercise, the FMV becomes your cost basis, because you already paid income tax on the spread. But brokers frequently report only the strike price on the 1099-B. File that unchanged and the IRS taxes the entire gain over the strike as a capital gain — taxing the bargain element a second time. The fix is to adjust the basis to the exercise-date FMV on Form 8949. Keep your exercise confirmation and the W-2 that shows the bargain element.
Short-term vs long-term after exercise
Once you exercise and hold the shares, the capital-gains clock starts on the exercise date. Sell within a year and any gain over the FMV is short-term, taxed at your ordinary rate. Hold more than a year and it is long-term, taxed at the preferential 0/15/20% federal rate. Because the ordinary-income tax is already settled at exercise, only the appreciation since exercise is affected by the holding period.
A quick example
You exercise 1,000 NSOs at a $2 strike when the FMV is $12. Your bargain element is ($12 − $2) × 1,000 = $10,000 of ordinary income. At a 32% marginal rate your employer withholds only 22% ($2,200), but you actually owe about $3,200 in federal income tax — a roughly $1,000 gap before FICA and state. Your cost basis is $12 per share. Sell a year later at $20 and your gain is only ($20 − $12) × 1,000 = $8,000. But if the broker reported a $2 basis, you would be taxed on $18,000 — paying tax again on the $10,000 you already reported at exercise.
Final word
NSOs are straightforward once you see the two events clearly: ordinary income at exercise, capital gains at sale. Two habits protect you — plan for the withholding gap so April is not a shock, and always correct your cost basis to the exercise-date FMV so you are never taxed twice. When the numbers are large, confirm them with a qualified tax professional.