Each February, Stripe waives its RSU second trigger. The settlement tax hits whether you sell or not.

What's publicly known

The tax event at settlement: what happened in February 2026

When Stripe waived the second trigger in the 2026 tender, vested RSUs settled. Here is the tax mechanics:

• Settlement income is ordinary income under IRC § 83.³ Each settled RSU was valued at the tender price (based on the $159B valuation), and the full settlement value entered your 2026 W-2 as supplemental wages — taxed at your top marginal rate. A meaningful RSU position at the 2026 tender price can represent a year or more of salary as a single W-2 event.
• Withholding was at 22% — your real rate is probably 35–37%. The IRS requires employers to withhold at the flat supplemental rate of 22% on supplemental wages under $1 million.⁴ If your marginal rate is 35–37% federal plus California's 13.3%, that 13–15 point federal gap — and the full state tax shortfall — is an April 2027 liability sitting unaddressed. Use the RSU settlement tax estimator to size the gap on your specific settlement amount and income level.
• FICA applies to the settlement income. Social Security tax (6.2% on wages up to $184,500 for 2026) applies if you haven't already passed the wage base. Medicare (1.45% + 0.9% Additional Medicare Tax on wages over $200,000 single / $250,000 MFJ) applies without cap. For high earners, FICA on a large settlement can add several thousand dollars the employer withholds but does not cover the income-tax gap.
• Settled but not sold = shares with carryover basis. If you settled RSUs but didn't sell them in the tender, you now hold Stripe shares with a cost basis equal to the settlement price. Future appreciation beyond that price is capital gain — long-term if held over one year from settlement date.

After settlement: selling now vs holding for capital gains

Once RSUs have settled (ordinary-income event done), the remaining decision is about the shares you now hold. This is a concentration decision, not a tax-minimization exercise — but tax treatment differs by timing:

• Selling within one year of settlement: short-term capital gain. The gain above your settlement-price basis is taxed at ordinary income rates — on top of the ordinary income you already recognized at settlement. Selling immediately in the tender avoids this (you sell at approximately basis), but selling newly-settled shares after a price appreciation before one year means the gain is ordinary too.
• Selling after one year: long-term capital gain. Gain above the settlement-price basis qualifies for the 2026 preferential LTCG rates (0%, 15%, or 20% depending on taxable income) plus 3.8% NIIT for single filers above $200,000 / MFJ above $250,000. The question is whether Stripe's valuation at a future tender is high enough to make the 12-month hold worthwhile against the concentration risk.
• The annual tender creates optionality each cycle. Because Stripe has run tenders in consecutive Februaries, employees can plan a paced glidepath — selling some portion each year to diversify concentration while preserving some upside. The concentration calculator can model the multi-year path from your current Stripe-heavy position to a target allocation.

The 7-year expiration clock

Most private-company RSU plans simply let unvested shares lapse if you leave before vesting. Stripe's reported 7-year expiration applies to vested RSUs that haven't been settled through a tender or IPO. This creates a hard deadline that generic equity planning ignores:

• 2019 grants expire ~2026. 2020 grants expire ~2027. If you received RSU grants in 2019–2020 and those shares haven't settled through a tender, the final window to realize value is approaching. Missing the last eligible tender before expiration can mean a total loss on fully-vested equity.
• The trigger-waiver is the unlock. Your vested RSUs only settle if Stripe waives the liquidity trigger (as it has done at each annual tender). If a year passes without a tender — or if you leave before a tender while outside the eligible former-employee window — those RSUs may never settle.
• Former employees have a narrower window. The reported 24–36 month former-employee eligibility window means that if you left Stripe in 2024, the 2027 tender (if it occurs) may be your last opportunity. Map your departure date against a 36-month lookback.

ISOs and NQSOs from early Stripe grants

Some Stripe employees — particularly those hired before the mid-2010s — may hold stock options alongside or instead of RSUs. The planning differs substantially:

• ISOs: exercise triggers AMT, not ordinary income (at exercise). The spread between your strike and the current 409A FMV is an AMT preference item at exercise — not regular income. Holding ISOs at a private company with no public price makes AMT exposure hard to model accurately, but each tender offer gives you a reference value. Use the ISO exercise and AMT calculator to size the exposure. AMT exemptions for 2026 are $90,100 single / $140,200 MFJ (OBBBA), phasing out at 50 cents per dollar above $613,150 / $1,226,300.
• NQSOs: spread at exercise is ordinary income. NQSO exercise locks in the spread as W-2 income plus FICA in the exercise year. The tender price provides a reference FMV; exercising in a tender year means the spread is known and cash from the tender sale can cover the tax. See the NQSO tax guide for the full mechanics.
• QSBS and Section 1202. Stripe was incorporated in 2010. By the time of its later funding rounds, the company almost certainly exceeded the $75 million gross-asset threshold that disqualifies stock from QSBS treatment under IRC § 1202.⁵ Most current Stripe equity will not qualify for the 50–100% Section 1202 exclusion. Early-2010s founders or angel-round holders may warrant a specific review with a tax attorney.

California and other high-tax states

Stripe is headquartered in South San Francisco; a large portion of its employee base is in California. This matters for settlement income:

• California treats RSU settlement income as ordinary income at top rates. California income tax goes up to 13.3% (12.3% above ~$625,000 single; 13.3% above $1 million).⁶ Unlike federal, California has no preferential LTCG rate — capital gains are taxed as ordinary income. This means the combined federal + California rate on RSU settlement and subsequent gains can exceed 50% for high earners.
• New York employees face similar exposure. New York City residents face state + city rates that can approach 12.7% combined — comparable in effect to California for large settlement events.
• Remote employees may have residency questions. Stripe's distributed workforce means many employees work in zero- or low-income-tax states. If you relocated from California and still have pre-relocation grant years, California may assert source-income taxation on RSU settlement income attributable to California-service periods. Multi-state allocation requires detailed work-location records.

Planning for the 2027 tender: the 12-month window

The 2026 tender closed in February. Based on the three-year annual pattern, the 2027 tender window would likely open in early 2027. That leaves approximately seven months of planning time — the longest period in the annual cycle:

• Estimated taxes from the 2026 settlement are due Q3 and Q4. If you have a withholding gap from the February 2026 RSU settlement, Q3 estimated tax is due September 15, 2026. The IRS safe harbor: pay at least 110% of your 2025 tax liability (if 2025 AGI exceeded $150,000) by year-end, split across Q3 and Q4 installments.⁷ Waiting until April 2027 on a large 2026 settlement gap will incur underpayment penalties.
• Decide how much to sell in 2027 before the window opens. Concentration decisions made under a 2-week tender window rarely reflect a considered plan. The time to set your sell percentage for the 2027 tender is now — defined by your target concentration, tax bracket, and the shares approaching the one-year LTCG holding period from the 2026 settlement date.
• Former employee eligibility. If you left Stripe in 2025 or 2026, confirm whether you fall within the reported 24–36 month former-employee window and whether your 2027 participation is at risk of lapsing.

Six planning steps for Stripe equity holders

1. Pull your full equity snapshot. Log into Carta or your equity portal and list every grant: RSUs (by year, number of units, settled vs unsettled, expiration date), options (strike price, type ISO vs NQSO, vested/unvested), and shares already held with their settlement-price basis. Note any grants from 2019–2020 approaching the 7-year clock.
2. Size the 2026 withholding gap and file Q3 estimates. If RSUs settled in the February 2026 tender, your employer withheld at 22% federal supplemental rate. Use the RSU settlement estimator to calculate the gap between withholding and your actual 2026 marginal rate. Make a Q3 estimated payment (IRS by September 15; California FTB by September 15) to reduce the April 2027 underpayment penalty exposure.
3. Model the 7-year clock on older grants. If you have 2019 or 2020 grants that haven't settled, assume the 2027 tender (if it runs) is your last practical opportunity. Build your 2027 participation decision around ensuring those grants settle before expiration, not around optimizing capital-gain holding periods you may not reach.
4. Set your target concentration before the 2027 window opens. Decide: what percentage of net worth do you want in Stripe after each annual tender? That number drives your sell sizing. Use the concentration calculator to model the 3–5-year glidepath from your current position to a target allocation. Do this in the next 30 days — not in the two weeks when the tender is live.
5. Check the one-year LTCG clock on 2026 settlement shares. RSUs that settled in the February 2026 tender have a cost basis at the February 2026 settlement price. Shares held past February 2027 qualify for long-term capital-gains treatment on any appreciation. If you're planning to sell in the 2027 tender anyway, holding to the one-year mark and getting LTCG treatment on the gain is often worthwhile — run the math with your actual marginal rate and projected Stripe valuation.
6. Get the modeling done by a specialist. Stripe's combination of double-trigger RSU settlement, 7-year expiration, annual tender cadence, and California state tax creates interactions that are difficult to model in generic tools. A fee-only fiduciary who works equity compensation can run the full scenario for your specific grant mix, income, and state — before the 2027 tender window forces a rushed decision.

Researching Stripe as an investor?

Stripe is private — there is no public ticker. Accredited investors sometimes access secondaries through specialized marketplaces with their own transfer restrictions, fees, and liquidity risks. We don't sell or arrange investments. This page is for employees and holders who already hold Stripe equity and are planning decisions around it.

The next tender opens in about seven months. Build the plan now.

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