1099-K reporting deadline 2026

If you are a payment settlement entity — which includes every marketplace operator, every franchise rollup that centrally processes, every agency that runs client funds through its Stripe — the 1099-K calendar in 2026 is tighter and more watched than last year. The IRS has invested in matching enforcement, the threshold is scheduled to step down further, and states keep layering their own earlier deadlines on top.

Here is the operator-facing calendar for the 2025 tax year (forms issued in early 2026), with the 2026 tax year (forms issued in early 2027) note at the end so you can plan.

1. The calendar for 2025 tax year forms

January 31, 2026: Forms 1099-K due to payees. If you are the payment settlement entity (PSE), every payee that hit the threshold needs their form by this date. Electronic delivery requires affirmative consent; default is paper.

February 28, 2026: Deadline for paper filing to the IRS if you are filing fewer than 10 forms total (across all 1099 types combined under the 10-form aggregate rule).

March 31, 2026: Deadline for electronic filing to the IRS. This is the operational deadline for most operators because anyone with 10+ combined 1099s must file electronically.

2. The threshold for 2025 tax year

$2,500 gross settlement volume is the federal 1099-K reporting threshold for tax year 2025 under the current transition schedule. Transaction count floor was eliminated in the 2022 American Rescue Plan amendments; gross amount alone now triggers filing.

3. What 2026 tax year looks like

$600 threshold takes effect for 2026 tax year transactions (forms issued January 2027) unless Congress extends the transition again. Operators should plan systems around $600 now rather than wait — backfilling TIN matching at $600 for a year of data is painful.

4. State overlays

Massachusetts and Vermont have $600 thresholds already. New Jersey has $1,000. Virginia has $600 for tax year 2025. Illinois uses federal thresholds but enforces strictly. Maryland, Arkansas, District of Columbia have their own schedules. If your payees span multiple states, you are filing to the lowest applicable threshold per state — the combinatorial headache is real.

5. Who is the PSE

The payment settlement entity is whoever has custody of the funds before they reach the payee. For Stripe Connect direct-charges, Stripe is the PSE. For Stripe Connect destination charges where the connected account owns the card charge, the connected account is the PSE. For your own merchant account that processes client funds (common in agencies, marketplaces, franchise rollups), you are the PSE. See marketplace reporting.

6. TIN matching — do it in Q4

The IRS's TIN Matching Program lets you verify payee TIN/name combinations against IRS records before you file. Mismatches trigger B-notices and backup withholding. Do the TIN matching sweep in October-November, not January. See TIN matching.

7. Box amounts that trip operators

Box 1a is gross payments — this includes refunded and disputed transactions, not net revenue. That is the number that ends up on the payee's 1099-K. Operators constantly report net and get B-notice mismatches with the payee's tax return.

8. Extension mechanics

Form 8809 grants a 30-day extension on the IRS filing deadline (March 31 -> April 30 for electronic filers). It is automatic for the first extension; second extension requires hardship justification. There is no extension available on the January 31 payee deadline without penalty.

9. Penalties

$60 per form if filed within 30 days of the deadline. $120 per form if filed by August 1. $310 per form if filed after August 1 or not at all. Intentional disregard: $630+ per form with no cap. For a multi-brand operator with 2,000 payees, missing by a month is $120k. Missing by a quarter is $620k.

10. Common late-Q1 mistakes

(a) Mailing forms to old addresses — update from your customer/vendor record system in December. (b) Missing state e-file thresholds — states do not follow federal paper/electronic breakpoints consistently. (c) Double-reporting because two entities in your stack each think they are the PSE. (d) Including refunded transactions in the wrong box.

11. Agency, marketplace, and franchise nuances

Each of these models has a different answer for "who owns the 1099-K." See the three playbooks: agency, marketplace, franchise.

12. Multi-brand operator pattern

If you run 8 brands on 4 Stripe accounts, you are getting four 1099-Ks. If you run them on an orchestration layer routed through a parent MID, you are potentially getting one 1099-K for the whole flow — but tax treatment of the internal transfers changes. Get your tax counsel involved before year end, not during.

2026 calendar cheat sheet

• Jan 31, 2026 — 1099-K to payees.
• Feb 28, 2026 — Paper filing to IRS (if under 10-form aggregate).
• Mar 31, 2026 — Electronic filing to IRS.
• Apr 30, 2026 — Extended deadline (with Form 8809).
• Throughout Q1 2026 — State deadlines stagger; check every state where you have payees.

Practical next steps

Run TIN matching in November. Audit which entity in your stack is the PSE for each flow. Confirm that reporting matches tax recognition. If you are not sure — because your Stripe Connect configuration is a mix of direct and destination charges — have counsel review before January. See pricing for the consolidated 1099-K reporting layer or apply and we will run the audit on your current stack.

13. Common filer errors that trigger B-notices

(a) Sending 1099-K to the entity that operates the business but filing under a different EIN. (b) Box 1a totals that include refunded transactions counted wrong. (c) TIN/name mismatches because payees changed entity mid-year. (d) Amounts reported in gross but reconciled net on tax return. Each error triggers an IRS matching notice that requires response.

14. Vendor selection for 1099 filing

Track1099, Tax1099, and Yearli lead the independent filer market. Stripe, Square, and PayPal file their own automatically for payees they settle. Multi-rail operators with aggregated volume usually need an independent filer to consolidate. Pricing runs $2-10 per form with volume discounts; budget $500-3,000 annually for mid-market.

15. State e-file participation

Combined Federal/State Filing (CF/SF) program covers most states but not all. Massachusetts, Oregon, Pennsylvania, and a handful of others require direct state e-file in addition to federal. If you have payees in those states, verify your filer supports the state-specific e-file schedule.