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Year-end & tax season checklist

Offices in Clackamas & The Dalles, Oregon

503-785-3200

Heather’s Tax Service & More

January

1099 deadlines for employers: 31 January is closer than you think

Form 1099-NEC is due to both recipients and the IRS by 31 January — earlier than almost everything else at year end, and the deadline most small businesses discover late.

Tax year 2025 (filed in 2026)

A bookkeeper working through a set of monthly accounts

Who needs one

  • Anyone you paid $2,000 or more for services during the year who is not an employee, for payments made in 2026 (the threshold was $600 through 2025)
  • Generally not payments to corporations — with exceptions, legal fees being the common one
  • Not payments made through a third-party settlement network such as a card processor or payment app; those are reported by the network on Form 1099-K

The bigger question underneath

Filing the 1099 is the easy part. Whether the person should have received a W-2 instead is the part that costs money, and it is decided by how the work was actually performed rather than by what the contract says. Oregon applies its own test for unemployment insurance, which can produce a different answer than the federal one. See 1099 contractor filing.

Penalties

Penalties for late information returns scale with how late they are, per form. On a business with fifteen contractors that adds up quickly, and an intentional disregard finding is considerably worse. Filing on time with an imperfect form generally beats filing a perfect one in March.

Not sure how this applies to you?

Call 503-785-3200 or schedule an appointment. We will find a time that works.

Katie Wells, bookkeeper

Written by

Katie Wells

Bookkeeper, 25+ years

Katie has kept books for small businesses for more than 25 years — QuickBooks, payroll, AP, AR, reconciliations and monthly reporting.

Reviewed by

Heather Perkins

Enrolled Agent, Oregon Licensed Tax Consultant

Last reviewed

This page is general information about Oregon, Washington and federal tax rules, not advice about your own return. Thresholds and rates change every year. Figures were verified as of August 2026 — check the linked official sources, or talk to us about your situation.

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