From the moment your employment ends, a quiet 90-day clock starts. If you do not exercise your vested options before it expires, the company keeps them. No grace period, no second notice, no exception for "I forgot." Here is exactly how the window works.
The 90 days are calendar days, counted from your termination date (usually your last day of employment, not the day you gave notice). The deadline is 90 days later at the close of business in your equity platform's time zone. If your last day is March 15, your window closes around June 13. If you have not exercised by that date, the vested options revert to the company.
A reminder set on your last day gives you the buffer to decide deliberately instead of in a panic.
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Most people leave a job thinking about their next chapter, not their old equity. The first few weeks after termination are about benefits paperwork, COBRA decisions, and the new job. Equity sits in the back of your mind as a vague intention you'll deal with "soon."
Then the math hits. To exercise, you need cash for the strike price, often tens of thousands of dollars. For incentive stock options at a private company, you may also owe Alternative Minimum Tax (AMT) on the spread between strike price and fair market value, sometimes more than the exercise cost itself. None of this is a 24-hour decision. You need a CPA, possibly a loan, and time to think clearly.
First-person accounts of forfeited equity routinely describe the same pattern: the holder knew about the deadline, kept meaning to address it, and discovered too late that the date had passed. The National Center for Employee Ownership notes that exercising vested options within the 90-day window is one of the most commonly missed steps in equity compensation.
Treat the 90 days as a project with phases, not a single deadline. Here is what each phase should cover.
Get your termination date in writing from HR. Pull your vested option count, strike price, and current fair market value from your equity platform. Confirm the exercise window length in your grant agreement, not in casual conversation.
A CPA with startup equity experience can model the AMT impact and compare exercise scenarios. This conversation alone takes a few weeks to schedule, hold, and incorporate. Do not skip it for grants worth more than a few thousand dollars.
Decide whether you have the cash, will use a non-recourse loan from ESO Fund or Secfi, or will partial-exercise. Lenders require diligence on the company and your equity, which takes one to three weeks.
Submit the exercise paperwork through your equity platform, wire the strike price, and confirm settlement. Get written confirmation from the company. Build in margin for processing delays.
If you have not exercised by this date, the vested options revert to the company. You cannot un-forfeit them. Document anything you did exercise for next year's tax return.
For options at a private company, the cost can be staggering. A grant with a $1 strike price and 50,000 vested shares costs $50,000 in cash just to exercise, plus possible five-figure AMT exposure. Many people leave private-company equity on the table because the cash isn't there.
Three real alternatives exist within the window:
Doing nothing is also an option. Just be clear-eyed that "do nothing" equals "forfeit everything."
Of every stock-options deadline, the 90-day post-termination window has the highest consequence-per-day-of-forgetting ratio. There is no fee for being late. There is no rescheduling. There is only the date and what you did before it.
See the full guide on stock options exercise reminders, or read about the tax implications of exercising before you make the call.
The default is 90 days from your last day of employment. Some companies extend the window to 1, 5, 7, or 10 years as part of their equity policy, but you have to confirm yours in your grant agreement or termination paperwork. The 90-day default is by far the most common.
Unvested options are forfeited immediately. Vested options enter your post-termination exercise window (typically 90 days). If you do not exercise within that window, the vested options also disappear. Resignation, layoff, and firing typically trigger the same clock, though some companies offer longer windows for layoffs.
IRS rules require that incentive stock options (ISOs) be exercised within three months of termination to retain ISO tax treatment. Most companies set the window at 90 days to match that rule. The window can legally be longer, but the options convert to non-qualified stock options (NSOs) after the 90-day mark and lose the preferential tax treatment.
Several options exist. Some companies allow cashless exercise (selling to cover the cost) once the stock is public. Specialized lenders like ESO Fund, Secfi, and others offer non-recourse loans for private company exercises. You can also exercise a partial amount you can afford and forfeit the rest. Doing nothing equals forfeiting everything.
Usually yes, but check your severance agreement and equity documents. Some companies extend the window for layoffs as a goodwill gesture or include it in severance packages, especially for senior employees. The default policy is still 90 days unless explicitly extended in writing.
It starts on your termination date, which is usually your last day of employment, not the day you give notice. Confirm the exact date with HR or in your separation letter. The 90 days are calendar days, not business days, so weekends and holidays count.
A free email reminder set on your last day buys you the time to decide deliberately. No account needed.
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