Is the Stripe tender offer taxable even if I don't sell?

Yes. When Stripe waives its RSU second trigger at the annual tender, vested RSUs settle into shares at the tender price — that settlement value is ordinary income under IRC § 83, reportable on your W-2, whether or not you elect to sell shares in the offer. The taxable event is settlement, not the sale.

What rate is the Stripe tender RSU settlement income taxed at?

At your top marginal ordinary income rate. Stripe withholds at the IRS flat supplemental rate (22% for amounts under $1 million), but if your combined federal bracket is 35–37% plus California's 13.3%, the withholding leaves a 13–29 percentage-point gap that becomes an estimated-tax liability for Q3 (September 15) and Q4 (January 15) of the settlement year.

How do I decide how much to sell in the Stripe tender?

Anchor the decision to a written concentration policy — the percentage of net worth you want in Stripe — not to a price prediction or expiration anxiety. Then layer in tax: shares already settled and held over one year from settlement date sell at long-term capital-gains rates (federal 20% max + NIIT, no CA preference), which may be worth preserving. Set the percentage before the window opens; two-week tender windows are not the time to model from scratch.

What happens to the 7-year RSU expiration at the tender?

A tender where Stripe waives the second trigger resets the clock for settled RSUs — the 7-year expiration applies to unvested or unresolved RSUs, not to shares already settled in a prior tender. Employees with 2019–2020 grants who have not yet had those RSUs settled through a tender are approaching the 7-year limit; if no tender (or IPO) occurs before expiration, those specific grants may expire worthless.

Do former Stripe employees qualify for the tender?

Reportedly, Stripe has included former employees within approximately 24–36 months of departure in past tender offers. The exact lookback window, eligible equity types, and participation mechanics are set in each year's official offer materials — verify before the window closes.

The Stripe tender settles your RSUs whether or not you sell

This is the feature that surprises most Stripe employees: when Stripe waives its RSU second trigger at the annual February tender, vested RSUs become shares and generate ordinary income at the tender price — regardless of your sell election. The tax event is settlement, not the sale. If you participate and sell, you receive cash and owe ordinary income tax. If you participate but hold, you receive shares and still owe ordinary income tax. Understanding this flow — before the window opens — is the foundation of any Stripe tender plan.

How the annual program has worked

Three consecutive years: 2024, February 2025, February 2026. Stripe has run employee tender offers annually, with the February 2026 offer reported at a $159 billion valuation — up ~74% from the ~$91.5B February 2025 tender. Both current and former employees (within ~24–36 months of departure) were reported eligible in recent years.¹
The second-trigger waiver is the mechanism. Stripe RSUs carry double-trigger vesting: service vesting plus a liquidity event. At each tender, Stripe reportedly waives the liquidity trigger for eligible employees, causing those RSUs to settle. This differs from Databricks, which removed its trigger entirely in 2025 — for Stripe, the tender IS the settlement event each time it runs.
No IPO is announced. Stripe leadership has described the company as "robustly profitable" (~$2.2B 2024 free cash flow) and not dependent on public markets. The base case for external observers is 2027 or later. Plan around the February tender cadence as the liquidity program.
Programs change — verify your documents. Eligibility, caps, trigger-waiver mechanics, and pricing are set in each year's official offer materials. Confirm against your equity portal, settlement statements, and offer documents before acting. Educational only; not affiliated with or endorsed by Stripe, Inc.

The tax flow at a Stripe tender

When the tender runs and Stripe waives the second trigger for your vested RSUs, here is what happens in sequence:

RSUs settle at the tender price → ordinary income. Each vested RSU converts to a share at the tender-offer price. The full settlement value is ordinary income under IRC § 83,² reported on your W-2 in the tender year. This happens for all eligible vested RSUs — not only the ones you elect to sell.
Employer withholds at 22% supplemental rate. The IRS flat supplemental withholding rate applies to supplemental wage payments under $1 million.³ For a $500K RSU settlement, employer withholding is ~$110K federal. If your marginal federal rate is 37% — common for senior Stripe employees in California — your real liability is ~$185K federal plus ~$66.5K California (13.3%). The withholding gap is roughly $141K in this scenario, due as estimated taxes.
You receive shares (and optionally sell some). After settlement, you hold shares with a cost basis equal to the settlement price. If you elect to sell shares in the tender window, those proceeds arrive net of normal transaction mechanics. The sale of shares at approximately their settlement-price basis generates minimal additional gain or loss.
Shares held beyond settlement carry a capital-gains clock. Any shares you hold past the settlement date start a holding period. Gain above the settlement-price basis is long-term capital gain — 0/15/20% federal (20% starts above $545,500 single / $613,700 MFJ in 2026) plus 3.8% NIIT above $200K single / $250K MFJ — if held more than one year. California taxes gains as ordinary income regardless of holding period.
Nothing is withheld on subsequent capital gains. If you sell settled shares in a future window or on the secondary market at a price above your settlement-date basis, those gains arrive gross. The estimated-tax obligation for that quarter — Q2 (June 15), Q3 (September 15), or Q4 (January 15) — falls to you.

Sizing how much to sell

Settlement is not a choice — it happens to all eligible vested RSUs. The only discretionary variable is how many settled shares to sell in the tender window versus hold. That decision has three inputs:

Concentration policy. What percentage of your total net worth do you want in Stripe after each tender? If Stripe represents 80% of net worth today and your policy is 50%, sell enough this tender to move toward that target. Use the concentration calculator to model the multi-year glidepath.
Holding-period tax. Shares settled in February 2026 cross the one-year LTCG mark in February 2027. If you plan to sell at the 2027 tender anyway, holding those February 2026 shares to February 2027 converts the gain on any price appreciation from ordinary income (up to 37% federal + 13.3% CA) to LTCG (20% federal, but still ordinary for CA). Run the math against your expected 2027 valuation and your specific marginal rates.
The 7-year expiration clock. Unsettled RSUs from 2019 or 2020 grants are approaching the 7-year expiration. For those specific grants, settlement via tender participation is not optional — it is the only path to value. Prioritize getting those grants settled before any price-optimization strategy for newer grants.

The 7-year expiration clock and tender urgency

Unlike most RSU plans, Stripe RSUs reportedly expire 7 years from grant date regardless of whether a liquidity event has occurred. This creates a hard deadline that generic equity planning ignores:

2019 grants → expiring ~2026. 2020 grants → expiring ~2027. If you received grants in these years and they have not settled through a tender, you are in or approaching the final window. Missing the last eligible tender before expiration can mean a total loss on fully-vested equity.
Former employee eligibility narrows the window further. Stripe's reported ~24–36 month former-employee eligibility window means a 2024 departure gives you only the 2025 and possibly 2026 tenders. Map your departure date against a 36-month lookback to determine your last eligible offer.
The trigger-waiver mechanism is Stripe's choice each year. If a year passes without a tender — or without a waiver — RSUs simply sit unresolved, with the expiration clock running. That makes participation in each offer a more urgent default for employees with aging grants than for employees with recently-issued grants.

Estimated taxes: the number most employees miss

The withholding gap from RSU settlement is the most common financial surprise at Stripe tender events. The February settlement creates a 2026 tax-year liability that falls across Q3 and Q4 estimated payments:

Q3 2026 (September 15) has passed. If your February 2026 RSU settlement created a withholding gap and you have not yet made estimated payments, you are already accumulating underpayment penalty interest (~7% annualized for Q3 2026 underpayments).
Q4 2026 (January 15, 2027) is the next deadline. You can still reduce exposure by making a Q4 estimated payment that brings your total 2026 payments to 110% of your 2025 tax liability (IRS safe harbor for AGI over $150K in 2025).⁴
Use the estimator. The RSU settlement tax estimator computes the gap between 22% supplemental withholding and your real marginal rate at any settlement amount, income level, and state.

Planning steps before the 2027 tender

Pull your full equity inventory. From your equity portal: every RSU grant (date, units, vested, settled, unsettled, expiration year), any options (ISO vs NQSO, strike, vested), and shares already held with settlement-price basis. Identify any 2019–2020 grants approaching the 7-year clock.
Size the 2026 withholding gap and make the Q4 estimated payment. Use the RSU settlement estimator. If your 2026 settlement left a gap, a January 15, 2027 payment (the Q4 deadline) can still partially offset underpayment penalties.
Write a concentration policy before the next window opens. Decide now: what percentage of net worth in Stripe is acceptable given a 2027-or-later listing horizon? Document the number. Two-week tender windows are not the time to make this decision from scratch.
Map the LTCG clock on 2026-settled shares. February 2026 settlement → February 2027 LTCG crossing. If you plan to sell at the 2027 tender, holding to February 2027 converts gain on any appreciation to long-term rates federally (though not in California). Factor this into your 2027 sell-percentage decision.
Handle 7-year-expiration grants first. For any 2019–2020 grants still unresolved: model the scenario where no 2027 tender runs or you are ineligible. Expiration of fully-vested equity is a worst case; treat those grants as a priority in your participation election.
Work with a specialist before the window. Stripe's double-trigger-waiver mechanics, the withholding gap math, the 7-year clock, and California's no-preference LTCG treatment create combinations that generic planning tools handle poorly. A fee-only fiduciary who works equity compensation can model your specific grant mix against multiple 2027 tender scenarios — before the window forces a rushed election.

The 2027 window is about seven months out. Build the plan now.

Get matched with a fee-only fiduciary who works Stripe tender cycles — RSU settlement taxes, withholding gap estimates, 7-year expiration prioritization, and multi-year concentration management. Free, no obligation.

Sources

CNBC — Stripe valued at $159 billion after tender offer for employees and shareholders (Feb 2026); annual cadence and former-employee eligibility per Stripe newsroom announcements and equity-comp adviser reporting.
IRC § 83 — Property Transferred in Connection with Performance of Services (Cornell LII) — RSU settlement as ordinary income at vesting.
IRS Topic 307 — Backup Withholding — 22% supplemental withholding rate on supplemental wages under $1M; IRS Rev. Proc. 2025-32 — 2026 ordinary income brackets (37% top) and LTCG thresholds ($545,500 single / $613,700 MFJ for 20% rate); California treatment per California FTB.
IRS Topic 306 — Penalty for Underpayment of Estimated Tax — 110% safe-harbor rule for prior-year AGI over $150K; Q4 deadline January 15, 2027.

Tax values are 2026 per IRS Rev. Proc. 2025-32: supplemental withholding 22% (under $1M), LTCG 20% above $545,500 single / $613,700 MFJ, NIIT 3.8% above $200K single / $250K MFJ, California top rate 13.3% (FTB). Stripe program details are from public reporting; official offer materials control. Content is educational only. Not affiliated with or endorsed by Stripe, Inc.