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Featured Oct 02, 2025 5 min read

W‑9s before you pay, 1099s before you file.

The cheapest control in the back office: collect a signed W‑9 at contract, not at January year‑end. A short operational note on the penalty regime, the OBBBA threshold change, and the workflow that prevents every painful reporting season.

A contractor hands a W-9 form to a tax professional beneath an IRS reference
This conversation happens every January. Collect the W-9 before it does.

Every January, a portion of our client conversations goes like this: "We need to issue 1099s, but I don't have W‑9s for half these vendors, and three of them are off payroll now, and two never responded to our email." The fix is operational, not technical. It requires treating the W‑9 as a contract prerequisite, not a reporting task.

Why this gets mishandled

The information return regime looks simple on paper — if you pay an unincorporated US vendor more than the threshold for services during the calendar year, you owe them and the IRS a Form 1099‑NEC by January 31. The friction is collecting the vendor information after the relationship has started, sometimes after it has ended.

Vendors who were responsive when you were about to pay them a $5,000 invoice are markedly less responsive when you are emailing in February about a form they see no benefit in completing. Meanwhile, the penalty for failure to file a correct information return has been climbing.

The new $2,000 threshold

The One Big Beautiful Bill Act raised the 1099‑NEC / 1099‑MISC reporting threshold from $600 to $2,000, effective for payments made in calendar year 2026 and later. The $600 floor — unchanged since 1954 — had been stuck in place for seventy years. The new threshold will index for inflation starting in 2027.

Two things to understand:

The $2,000 threshold is welcome, but it does not reduce the need for a clean W‑9 on file. You still need to know whether a vendor is a corporation or a sole proprietor before you cut the first check.

The workflow that prevents January pain

The rule we apply to every client:

  1. W‑9 before the first payment. No W‑9, no invoice payment. Exceptions are rare and should be escalated, not routine.
  2. Store the W‑9 with the vendor master. Not in an email folder. Not on a shared drive without an index. In your accounting system's vendor record, scanned and attached.
  3. Re‑certify every three years. The W‑9 does not expire, but a lot can change: ownership structure, EIN, address, filing status.
  4. Flag foreign vendors early. Non‑US vendors need W‑8BEN or W‑8BEN‑E, not W‑9, and the withholding posture is very different.

Penalty regime

Penalties for failure to file a correct information return, for 2025 filings:

The penalty is doubled — once for the IRS copy, once for the payee copy. A hundred missing 1099s in the "intentional disregard" bucket is a $136,000 exposure. For most small businesses this is the single largest avoidable compliance liability on the books.

Backup withholding

If a vendor refuses to provide a W‑9, or the TIN they provided does not match IRS records, you are required to withhold 24% of subsequent payments and remit to the IRS on Form 945. This is the hammer. We rarely see it invoked — the threat is usually enough.

Practical tips

Three things that make the January turn painless:

The return on a disciplined AP workflow is boring and substantial: no penalty exposure, no January crunch, no awkward emails to former vendors. Worth the one afternoon of setup.

What we do

We audit AP workflows, set up vendor onboarding, and file 1099s at scale.

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