When Stripe runs an employee tender, vested double-trigger RSUs settle and their full value is taxed as W-2 wage income in that year, whether or not the employee sells, with federal withholding at 22% (37% once supplemental wages pass $1 million). Shares already held and sold at a gain are taxed separately, as capital gains.

Key takeaways

Under IRS Publication 15 for 2026, the federal withholding rate on supplemental wages such as settled RSUs is 22%, rising to 37% only on amounts above $1 million in a calendar year.
Only capital gains can be deferred into a qualified opportunity fund; the IRS states that ordinary gain is not eligible, so RSU settlement income never qualifies.
A tender year at a double-trigger company holds a wage slice that only deductions can reduce and a capital-gain slice that only deferral can touch, and the two need different tools.

Why does a Stripe tender create taxable income even if you don't sell?

Because at a double-trigger company the tender is the second trigger. Stripe's RSUs, as described in third-party planning guides, vest over four years with a one-year cliff but do not settle into shares until a liquidity event, and they expire seven years after grant if none occurs. When Stripe opens a tender and waives the liquidity condition for vested units, those units settle. Settlement, not sale, is the taxable moment.

From there the mechanics are the same as any RSU: the fair market value on the delivery date is compensation on the W-2, taxed at ordinary rates plus payroll taxes. The difference at a private company is that several years of vesting can settle at once. The single-trigger and double-trigger RSUs distinction decides whether the tender is a tax event at all; this piece assumes double-trigger.

So an employee who does not sell can still owe tax on every vested unit that settled, with no cash from the event to pay it, and an employee who does sell has two transactions on the same day: the settlement (wages) and, for shares acquired earlier, the sale (capital gain or loss).

What is the wage slice, and what can reduce it?

The wage slice is every RSU that settles because of the tender. It is ordinary income, and no deferral vehicle applies to it. Only deductions and the timing of other income can change the tax on it.

Take an illustrative engineer at a late-stage fintech, single, $250,000 salary, with 4,000 vested double-trigger RSUs that settle in a tender at a hypothetical $150 per unit. That is $600,000 of W-2 income in the tender year, on top of salary. For 2026 the 37% federal bracket begins at $640,600 of taxable income for a single filer and the standard deduction is $16,100, so most of that $600,000 is taxed at 35% and 37% federal, before state tax. The incremental federal income tax on the settlement works out to roughly $213,000.

Payroll will not withhold that much. The supplemental wages are under $1 million, so the employer withholds 22% federal, about $132,000, leaving a gap near $81,000 before state tax that the employee covers through estimated payments or a reserve. That gap is a cash-flow problem, not a strategy; the planning is what happens to the slice itself.

Three levers act on the wage slice, and only three:

Deductions landed in the same year. The largest one most employees can create in a peak-income year is charitable. Funding a donor-advised fund with long-held appreciated assets deducts their fair market value, up to 30% of adjusted gross income for appreciated property (60% for cash), and the embedded gain is never taxed. For 2026, gifts are deductible only above a floor of 0.5% of AGI, and itemized deductions for top-bracket taxpayers are worth at most 35 cents per dollar, so a $100,000 gift of appreciated index shares on a $1.05 million AGI deducts about $94,750 and is worth roughly $33,000 federal. Give old, appreciated positions, never the units that just settled; see why donating shares that just settled saves nothing.
Retirement deferrals already available. The 401(k) employee limit and any after-tax room the plan allows shelter a little, not a six-figure settlement.
Timing of other income. An option exercise, a Roth conversion or a deferrable bonus usually should not share the tender year.

Nothing on this list defers the wage slice. That is what readers most often get wrong when they hear “opportunity zone” in the same breath as “tender”.

What is the capital-gain slice, and what can defer it?

The capital-gain slice is the gain on shares the employee already owned before the tender: units that settled in an earlier liquidity event, or options exercised in a prior year. Sold into the tender at a higher price, the difference between the sale price and the cost basis is a capital gain, long-term if held more than a year.

Returning to the illustration: the same engineer also holds 2,000 shares that settled in an earlier event with a basis of $50. Selling them at $150 produces a $200,000 long-term capital gain. At the 20% federal rate plus the 3.8% net investment income tax, which applies above $200,000 of modified AGI for a single filer, that slice carries about $47,600 of federal tax.

This is the only slice a qualified opportunity fund can touch. Under the IRS Opportunity Zones FAQ, eligible gains are capital gains and qualified Section 1231 gains, the investment must generally be made within 180 days of the sale, and ordinary gain is not eligible. The rules are also changing. Gains deferred under the original program must be recognized no later than December 31, 2026 and cannot be redeferred. For amounts invested after that date, IRS Notice 2026-40 describes a rolling five-year deferral with a 10% basis step-up after five years (30% for qualified rural opportunity funds) and new zone designations from January 1, 2027; a gain realized in late 2026 can still use the new rules if the investment is made on or after January 1, 2027 inside its 180-day window.

The test before anyone opens a QOF account is simple: how large is the capital-gain slice? If everything sold in the tender settled in the tender itself, basis equals sale price, the gain is near zero, and there is nothing to defer. The $600,000 wage slice in the example is entirely outside its reach.

How do the two slices compare side by side?

Wage slice

What it is: vested double-trigger RSUs that settle because of the tender
Tax character: ordinary income on the W-2, plus payroll taxes
2026 top federal rate: 37% above $640,600 taxable income (single)
Withholding: 22% federal supplemental; 37% above $1 million
Can a QOF defer it? No; ordinary gain is not eligible
What reduces it: same-year deductions (DAF funded with appreciated assets), retirement deferrals, moving other income out of the year
Illustrative size in the example: $600,000

Capital-gain slice

What it is: gain on shares already owned (prior settlements, prior exercises) sold into the tender
Tax character: capital gain; long-term if held over a year
2026 top federal rate: 20% plus 3.8% NIIT above $200,000 MAGI (single)
Withholding: none; covered by estimated payments
Can a QOF defer it? Yes, within 180 days, under the rules for the investment date
What reduces it: lot selection, loss harvesting, deferral, holding period
Illustrative size in the example: $200,000

Is a tender sale ever taxed as wages even on old shares?

Sometimes, when the tender is compensatory. If an employer-arranged tender pays more than the company's current fair market value (its 409A valuation), the IRS can treat the excess as compensation to employees who sell, taxed as wages rather than capital gain; a tender priced at or below the 409A value is generally non-compensatory. The tender notice usually says which it is. This changes the size of each slice, not the framework: a compensatory premium moves dollars from the capital-gain slice into the wage slice.

What should an employee check before a tender window closes?

Sort every unit and share into its slice. Vested units that will settle because of the tender go in the wage slice. Shares with a basis from an earlier settlement or exercise go in the capital-gain slice, with lot dates and basis.
Size the wage slice at the marginal rate, not the withholding rate. The 22% withheld is a floor; for most participants the real federal rate on the slice is 35% to 37%, before state tax. Reserve the difference or schedule an estimated payment tied to the settlement date.
Decide the charitable question in the same tax year. A DAF contribution has to land by December 31 of the tender year, funded with the oldest, most appreciated positions.
Measure the capital-gain slice before considering a QOF. If the gain is small, deferral is the wrong tool; if it is large, the 180-day clock starts on the sale date.
Read the tender notice for the compensatory question.

Employees who start with the vehicle (“should I do an opportunity zone fund?”) usually learn afterwards that their gain was mostly wages. Employees who start with the sort find the right tool for each slice, as happened for a Cerebras engineer whose double-trigger RSUs settled on IPO day, where the settlement and the later sales were planned as separate events.

The bottom line

A tender at a double-trigger company such as Stripe is two taxable events wearing one wire transfer. The settlement of vested RSUs is wages, taxed in the tender year whether or not a single share is sold, and only deductions can reduce it. The sale of shares acquired earlier is a capital gain, and only that slice can be deferred. Pointing each tool at the slice it can actually reach is coordination that sits between a CPA who sees the W-2 in March and a brokerage advisor who sees the trade confirmation in February. Alphanso Inc is a flat-fee fiduciary wealth advisory for employees with equity compensation (RSUs, ISOs, NSOs and ESPP); advisors are paid a flat annual fee, never a percentage of assets or commissions. If a tender is on the horizon and nobody has sorted the slices yet, book a call and the team will model both before the window opens.

FAQ

Do I pay tax on my Stripe RSUs when they vest or when the tender happens? At the tender. Double-trigger RSUs are not taxed on the vest date because the shares are not delivered then. When a tender waives the liquidity condition and vested units settle, their full value is taxed as ordinary income in that year. This applies to the vested units that settle, not only to the ones sold.

If I don't sell in the tender, do I still owe tax? Yes, at a double-trigger company, on every vested unit that settles because of the tender. The employee holds shares and owes income tax on their settlement-date value with no sale proceeds to cover it, which is why many participants sell at least enough to fund the tax.

Is the money from a tender offer capital gains or ordinary income? Both, depending on which shares. Units settling because of the tender are ordinary income on the W-2. Shares the employee already owned from an earlier settlement or exercise, sold at a profit, produce a capital gain, long-term if held more than a year. A compensatory premium above fair market value can be reclassified as wages.

Can I put tender proceeds into an opportunity zone fund to defer the tax? Only the capital-gain portion. The IRS limits qualified opportunity fund deferral to capital gains and qualified Section 1231 gains, invested within 180 days; ordinary gain is not eligible. RSU settlement income from the tender cannot be deferred this way, and for investments after December 31, 2026 the deferral runs five years under the new rules.

How much federal tax is withheld when private company RSUs settle in a tender? 22% on supplemental wages up to $1 million in the calendar year, and 37% on the excess, under IRS Publication 15 for 2026. Employees whose marginal rate is higher than the rate withheld make up the difference through estimated payments or at filing.

This content is for educational purposes only and does not constitute personalized financial, tax or legal advice. Tax services are for educational purposes and do not constitute legal advice. Figures reflect 2026 federal rules as published by the IRS and may change; individual circumstances vary. All dollar examples are hypothetical. Alphanso Inc is a registered investment adviser; registration does not imply a certain level of skill.