How do OpenAI tender offers work?

Periodically, outside investors offer to buy shares (historically PPUs) from current and former employees at a negotiated valuation — an investor-led secondary. OpenAI sets eligibility, per-person caps, and windows in each offer's materials. The October 2025 window was reported at roughly $6.6 billion across 600+ people with a $30 million per-person cap.

When is the next OpenAI tender offer?

Not announced. OpenAI has run a series of investor-led secondaries, most recently the large October 2025 window. With an S-1 filed but IPO timing undecided — possibly 2027 — a further tender before listing is plausible but not guaranteed. Eligibility and terms only become real when official offer materials arrive.

How are OpenAI tender sales taxed?

Sale proceeds are taxed like a sale of the underlying equity: gain over your cost basis, long-term if your holding period exceeds one year, short-term (ordinary rates) if not. The PPU-to-PBC-share conversion reportedly preserved basis and holding periods. Because withholding generally doesn't cover capital gains, most sellers owe estimated taxes for the quarter of the sale. Grant-specific terms and 83(b) history can change the analysis — confirm with a CPA.

Should I sell in an OpenAI tender or wait for the IPO?

That's a concentration decision, not a prediction contest. Tender pricing has historically sat below later round marks — but paper marks aren't realized gains, lockups delay IPO liquidity, and single-stock concentration is real risk. A common framework: decide what percentage of net worth you want in OpenAI long-term, and use the tender to move toward that number rather than betting all-or-nothing on the listing.

OpenAI tender offers: the liquidity program while the IPO waits

Until OpenAI lists — late 2026, 2027, whenever — tenders are how employee equity becomes money. The last big window moved ~$6.6 billion for 600+ current and former employees. Here's how the program has worked, how sales are taxed, and how to size participation if another window opens.¹

The tender track record

October 2025: ~$6.6 billion. The largest of a series of investor-led secondaries — 600+ current and former employees eligible, per-person cap reported raised to $30 million. Conducted at valuations materially below the later ~$852B round.¹
A recurring pattern, not a schedule. OpenAI's secondaries have been periodic and investor-led; there is no announced cadence, and each window's eligibility, caps, and pricing live in that offer's materials.
The instrument evolved mid-program. Historical windows involved PPUs; after the October 2025 PBC restructuring, holders reportedly hold converted PBC shares with basis and holding periods carried over.²
Programs change — verify your documents. Nothing here substitutes for the official offer materials, your equity portal, and your grant agreements.

Educational only; not affiliated with, sponsored by, or endorsed by OpenAI.

How a window actually works

Announcement and eligibility. The company notifies eligible holders — historically both current and former employees — with pricing, caps, and deadlines.
Pricing vs the headline valuation. Tender prices are negotiated with the buying investors and have historically sat below the next primary-round mark. That's the cost of liquidity now versus paper later — the tender guide covers the pricing-vs-409A mechanics.
Election. You choose how much to sell within your cap. This is the decision that deserves modeling, not instinct.
Settlement and taxes. Proceeds land; withholding on capital gains generally doesn't — see below.

The tax math

Gain = proceeds − basis. Basis is typically $0 (83(b) at grant) or the value recognized at earlier taxable events, carried through the PBC conversion per public reporting.²^,³
Holding period sets the rate. Over one year: long-term capital gains — 0%, 15%, or 20% federal (the 20% bracket starts above $545,500 single / $613,700 MFJ for 2026), plus 3.8% NIIT above $200K/$250K MAGI.⁴ One year or less: ordinary rates up to 37%. California taxes both identically, up to 13.3%.
Withholding won't save you. Capital-gain sales generally come with no automatic withholding — the quarter's estimated payment is on you. A large tender sale in, say, Q4 means a big January 15 payment.
Run your numbers. The OpenAI PPU & share sale tax calculator models ordinary vs long-term treatment, the 2026 brackets, NIIT, and your state rate.

Sizing: the only framework that survives hindsight

Every OpenAI holder who sold in a past tender "lost money" against the next mark — and every one of them also converted concentrated, illiquid, single-company risk into realized wealth. Both facts are true. The framework that works: write a concentration target (what % of net worth in OpenAI is right for you long-term), then use each window to move toward it. Selling to a policy converts hindsight into noise. The employee guide and tender guide go deeper; if the IPO firms up first, the IPO page covers what changes.

A window is short when it opens. Plan before it does.

Get matched with a fee-only fiduciary who works tender events — sizing against a concentration policy, basis reconstruction, estimated taxes, and multi-year planning. Free, no obligation.

Sources

CNBC — OpenAI confidentially files for IPO (June 8, 2026) — S-1 status and secondary-market history context; tender figures per public reporting compiled on Forge — OpenAI IPO timeline.
levels.fyi — How OpenAI's PPU equity compensation works — PPU mechanics and conversion reporting.
IRC § 83 and IRS Publication 525 — taxation of restricted property and dispositions.
IRS Rev. Proc. 2025-32 — 2026 long-term capital gains thresholds and ordinary brackets; NIIT per IRC § 1411. California treatment per California FTB.

Tender history reflects public reporting as of August 17, 2026; each window's official offer materials control. Tax figures verified against IRS Rev. Proc. 2025-32 for tax year 2026.