They are forfeited on your last working day in almost every plan. There is rarely discretion and rarely negotiation. A cliff you were weeks short of gives you nothing, which is why a resignation date near a vesting date is worth checking before you set it.

Whatever the plan says, commonly ninety days from the last working day. Some plans allow thirty, some allow several years. It is in the plan document rather than the offer letter, and it is absolute — options that expire are gone with no appeal.

In some plans yes, in others the clock stops at resignation. Where a vesting date falls inside a notice period this is worth establishing early, because it can be the difference between a tranche vesting and being forfeited.

Yes. The perquisite tax falls due at exercise regardless of whether any market exists for the shares. For an unlisted company that means a real cash bill against an asset you may not be able to convert for years. It is the central difficulty of leaving a startup with options.

Usually your final settlement. The employer deducts the perquisite tax at source, which can leave a last payment that is far smaller than expected, or nothing at all. Plan the exit assuming the final settlement will be substantially absorbed.

Only where a market exists to sell into, which for a listed company usually means yes and for an unlisted one usually means no. Some companies arrange a facilitated sale alongside a buyback. Without that, you need the full amount in cash.

A provision that penalises certain departures, typically dismissal for cause. It can forfeit even vested options, which most employees do not expect and never check. The definition of cause is drafted by the company and is worth reading while things are amicable.

As dividend income in your hands at your slab rate, on the full amount received, with no deduction for what the shares cost you. The cost is instead treated as a capital loss, useful only if you have capital gains to absorb it. This changed in October 2024 and a good deal of older material still describes the previous treatment.

Usually, on tax. A sale to a third party is a capital gain, where your cost is deducted and long-term rates may apply. A buyback taxes the gross amount at slab rates. Same price per share, materially different outcome — though a buyback may be the only liquidity actually on offer.

Occasionally, and it costs nothing to ask while you are still on good terms. Some companies extend windows for long-serving employees or where the departure is amicable. Ask before the resignation is formalised rather than after, when there is no leverage and no reason to accommodate you.

Most plans accelerate vesting and extend the window for the legal heir or nominee. The perquisite is still taxable, which means a family may face an exercise decision and a tax bill during probate, often without the cash and without understanding the deadline. It is the case that most needs planning in advance.

Usually much better. Plans commonly accelerate unvested options on retirement and extend the exercise window considerably. Whether you qualify depends on the plan's own definition of retirement age, which may not match the statutory one.

It depends entirely on the transaction documents. Options may be cashed out, exchanged for options in the acquirer, or accelerated. The tax follows whichever mechanism applies, and a cash-out is generally treated as a perquisite. Get the treatment in writing before signing anything.

The honest answer is that it is a risk decision rather than a tax one. Exercising converts a free option into a cash cost plus a tax bill, in exchange for an illiquid holding in a company you have just left. Where the company's prospects are uncertain, letting options lapse is a legitimate choice rather than a failure.

Most plans allow partial exercise, which is often the sensible answer where cash is the constraint. It lets you take a position proportionate to what you can fund and what you believe, rather than an all-or-nothing decision inside ninety days.

The exact number of vested options, the exercise price, the precise end date of the window, the current fair market value used for the perquisite, and how the tax will be collected. All five are things the company knows and will confirm while you are still an employee, and are far harder to extract afterwards.