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Morkel Financial & Tax Services

Exercising ISOs After a Layoff: The Cheap Year Is Usually Out of Reach.

By Ewan Morkel, EA6 min read

The year after a layoff is the cheapest year you will ever have to exercise incentive stock options, and §422(a)(2) puts it out of reach unless you were let go in the fourth quarter. On a $180,000 spread, that calendar accident is worth $9,714.

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A staff engineer gets the call on November 13. Severance runs twelve weeks, the badge stops working Friday, and buried in the packet is a line about 15,000 vested incentive stock options at a $3.00 strike against a $15.00 share price. The question isn't whether to exercise. It's which calendar year to do it in, because exercising ISOs after a layoff is one of the few places a ten-week delay is worth $9,714.

Why the gap year is cheap

Exercising ISOs after a layoff costs less because the spread has nothing to stack on.

Two rules do the work. Under §421(a) you recognize no regular taxable income when you exercise an ISO and hold the shares, so the spread never reaches your adjusted gross income. Under §56(b)(3) that same spread is an adjustment in computing alternative minimum taxable income, reported on Form 6251, line 2i, in the year your rights in the stock become transferable or stop being subject to a substantial risk of forfeiture.

The AMT you pay is the amount by which your tentative minimum tax (what the AMT system computes on its own) exceeds your regular tax, and salary moves both halves of that subtraction in opposite directions. It raises the regular tax, which is the credit against the tentative minimum tax. It also sits underneath the spread inside AMTI and pushes more of that spread out of the 26% rate and into the 28% rate, which for 2026 begins at $244,500 of taxable excess. In a year with a paycheck, the second effect wins. Above $500,000 of AMTI a second cliff opens, where the $90,100 exemption disappears at 50 cents on the dollar, and how many ISOs you can exercise without AMT prices that band.

The clock

Three months after your last day, the option stops being an ISO.

§422(a)(2) requires that you be an employee of the granting corporation at all times from the date of grant through the day three months before exercise. Miss it and the spread is ordinary wage income in the year you exercise, with withholding and payroll tax on top. §422(c)(6) stretches the window to twelve months for a disability separation, and death has no limit. Nothing else does, so the cheap year isn't a planning choice. It's a function of the month you were let go.

  • Last day between January and September. The three-month window closes inside the same year your salary and severance landed, so the cheap year is unreachable as an ISO.
  • Last day between October and December. The window crosses January 1, and this is the only configuration where the empty year and the ISO clock overlap.
  • An extended post-termination window of seven or ten years. Useful for cash flow, irrelevant here. The plan can hold the option open, but it cannot keep it an ISO, because §422(a)(2) is statutory.
The same 15,000 options, exercised ten weeks apart
Spread at exercise (15,000 × $12.00)
$180,000
2026 income: wages plus $60,000 severance
$275,000
2026 regular tax, no exercise
$59,384
AMT if exercised in December 2026
$37,898
2027 income: unemployment compensation
$20,000
2027 regular tax, no exercise
$390
AMT if exercised in February 2027
$28,184
Saved by waiting ten weeks
$9,714

Single filer, federal only, shares held past year end in both cases. 2026 figures from Rev. Proc. 2025-32: standard deduction $16,100, AMT exemption $90,100 phasing out above $500,000 of AMTI, 26% on the first $244,500 of taxable excess and 28% above it. The 2027 inflation adjustments were still unpublished on November 4, 2026, so the 2027 rows use 2026 amounts, which understates the gap.

The collision

A Roth conversion in the same year costs you the health insurance subsidy. The exercise does not.

The gap year has one set of empty brackets and two good uses for them. Most of what gets written about low-income years is about the other one, converting traditional retirement money to Roth. Both moves want the same year, only one is visible to the health insurance marketplace, and almost nobody notices which.

Household income under §36B(d)(2)(B) is modified adjusted gross income, which adds back only excluded foreign earned income, tax-exempt interest, and the nontaxable part of Social Security. An AMT adjustment is not on that list and never reaches AGI. A $180,000 ISO exercise moves your premium tax credit by zero dollars. A Roth conversion moves it by every dollar converted.

That matters more in 2026 than it has in five years. The enhanced subsidies expired at the end of 2025, so the 400% poverty-line ceiling is back, which for one person on 2026 coverage is $62,600 of household income. One dollar past it and the credit is zero. Section 71305 of the One Big Beautiful Bill Act then repealed the repayment caps in §36B(f)(2)(B), so the whole year of advance payments comes back instead of stopping at $1,625. Excess premium tax credit repayment in 2026 has the rest of it.

One exception runs the other way. §56(b)(3) requires no adjustment if you dispose of the stock in the same year you exercise. Sell inside the calendar year and the AMT item vanishes, but the disqualifying disposition puts the spread in Box 1 of a W-2 and in AGI, where §36B can see all of it. Exercise and hold is invisible to the marketplace. Exercise and sell is not.

Where I land

Size the exercise to the room, not to the option count.

The number worth knowing is not the tax on the whole grant. It's how much spread you can run through before any AMT starts. On $275,000 of income that crossover sits at $43,500, which is 3,625 of these options. On $20,000 of unemployment it sits at $71,600, which is 5,966. The empty year does not shave a few percent off the bill. It gives you 65% more free room.

So if your last day falls in the fourth quarter, wait. Ten weeks for $9,714 is the best-paid stretch of the whole layoff, and the only cost is a calendar reminder. If your last day was in March, the cheap year is gone, and the honest answer is usually to exercise less than you planned, or nothing. Funding a $37,898 AMT bill out of severance you may need for rent, to buy more stock in the company that just laid you off, isn't a tax strategy.

The AMT does come back. It's a §53 minimum tax credit claimed on Form 8801, and I walked the recovery in the AMT credit for an ISO exercise. What people underestimate is the wait, because the credit releases only in a year when regular tax exceeds tentative minimum tax, which means a year when you're employed again. The rest of that separation packet is in what happens to your RSUs when you are laid off.

Frequently asked

Quick answers on this topic.

My company gave me a 10-year window to exercise. Doesn't that solve this?

It solves the cash problem, not the tax one. A plan can hold the option open as long as it likes, but §422(a)(2) is in the statute and the company cannot waive it. Anything you exercise more than three months after your last day is a nonqualified option, so the spread is ordinary wage income in the year of exercise instead of an AMT adjustment, and payroll tax applies. The extended window is still worth having. It just isn't an extension of ISO treatment.

Is deliberately waiting for a low-income year to exercise an audit risk?

No. Choosing when to exercise an option is not a reportable position, and there is nothing to disclose. Your employer files Form 3921 for the exercise in whichever year it happens, and you report the adjustment on Form 6251 for that same year. What actually draws a notice is the opposite: a Form 3921 on file with no Form 6251 behind it, which is the most common ISO error I see in second-opinion reviews.

Do I have to make an estimated payment for the AMT, or can I wait until April?

You owe it during the year. §6654 measures the underpayment against your total tax, and the AMT is part of total tax, so a fourth-quarter exercise creates a Q4 estimate due January 15. Nothing is withheld on an ISO exercise, because no wages were paid. If you're leaning on the prior-year safe harbor, remember that the layoff year's tax is the figure that sets it, which is good news in the gap year and bad news in the severance year.

What happens if I exercise and the stock falls before I sell?

The AMT is computed on the fair market value on the exercise date and does not shrink when the price does. That's the risk you're taking on, and it's the reason to size the exercise to your AMT-free room rather than to the full grant. Two things soften it later. Your AMT basis in the shares is higher than your regular basis by the amount of the adjustment, so the AMT gain on a sale is smaller, and the §53 credit survives indefinitely until a year of regular tax releases it.

Can I still use the gap year if I start a new job in January?

The three-month clock runs from the end of your employment with the company that granted the options, so a new employer does not shorten it. The new salary is the problem. It refills the AMT room the empty year was supposed to give you, and a January start date can move the crossover back toward the $43,500 figure before you exercise a single option. If you have an offer in hand, run the exercise against the new income, not against the unemployment.

Equity compensation planning

Planning the exercise before you click buy.

ISOs, RSUs, ESPP shares, and 83(b) elections create tax the moment they vest or exercise, and the AMT bill can land months later. We model the spread, time the sales, and file the elections on the clock, so the windfall is not eaten by a surprise in April.

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