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Year-end & tax season checklist

Offices in Clackamas & The Dalles, Oregon

503-785-3200

Heather’s Tax Service & More

One post a week, scheduled against the tax calendar

Notes on Oregon, Portland and cross-border tax

Written to answer one question properly, published ahead of the month people start searching for it, and reviewed each January when the figures change.

Tulips in bloom in the Willamette Valley

Published

January 8, 2026 · Pam Wagner

When will I get my W-2, and what if it never arrives?

Employers must furnish W-2s by 31 January. What to do if yours has not arrived, is wrong, or belongs to a job you left.

Read January 15, 2026 · Katie Wells

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

Form 1099-NEC is due to recipients and the IRS by 31 January. What to file, who needs one, and why the penalties scale so quickly.

Read February 5, 2026 · Pam Wagner

Where’s my refund? How the IRS and Oregon actually process them

How long refunds actually take, why some are held by law, and what the IRS refund tracker is really telling you.

Read February 12, 2026 · Heather Perkins

The Oregon kicker, explained without the politics

What the Oregon kicker is, how the percentage is applied to your prior-year liability, and why it is a credit rather than a check.

Read March 2, 2026 · Heather Perkins

15 March: the deadline most business owners forget

S-corporation and partnership returns are due a month before individual returns. What that means for your K-1, and what an extension does and does not buy you.

Read April 1, 2026 · Heather Perkins

What the 15 April deadline actually covers in Portland

Seven separate filings land on 15 April for a Portland household. Here is the full list, including the local ones nobody aggregates.

Read

What is coming

The rest of the year’s calendar. Each of these is scheduled to publish ahead of the month people start searching for it — the extension post lands in September, not on 14 October.

January

  • Your tax document checklist for this season
  • Missed a quarterly estimate? What 15 January can still fix

February

  • You got a 1099-K. Now what?
  • Earned Income Tax Credit: who actually qualifies

March

  • Understanding your K-1, line by line
  • Bookkeeping cleanup before filing: what actually has to be right
  • Extension vs payment: what an extension does not buy you

April

  • The Portland Arts Tax: $35, and the penalty that is not
  • Cannot pay your tax bill? Your actual options
  • Metro SHS and Preschool for All: due dates and how to file

May

  • You got an IRS notice. Read this before you call them
  • When amending a return is worth it, and when it is not
  • LLC or S-corp for next year? Run it now, not in December
  • Recovering over-withheld Oregon tax: the Vancouver refund

June

  • Q2 estimates: the payment that catches people out
  • The freelancer mid-year check: six numbers to look at
  • Three bookkeeping habits that make next April short
  • Hiring your first employee in Oregon: the whole checklist

July

  • Paid Leave Oregon: what employers actually have to do
  • Reasonable compensation: the number the IRS actually litigates
  • Mileage logs that survive an audit
  • Metro SHS employer withholding: the duty most employers missed

August

  • Moving Oregon to Washington: the date matters more than you think
  • The remote-work withholding check-up, in ten minutes
  • Back tax resolution: what the process actually looks like
  • How to track hybrid workdays without thinking about it

September

  • Q3 estimates and the annualised income method
  • The extended S-corp deadline: 15 September
  • Year-end planning starts in September, not December
  • Notices and appeals: the deadlines you cannot get back

October

  • 15 October: the extended deadline, and what it does not extend
  • Missed the October deadline? Here is the order to do things in
  • Q4 planning: the moves still available to you
  • Changing entity type: why the timing is the whole decision

November

  • Retirement contributions: the biggest lever most people do not pull
  • Loss harvesting, and the wash-sale rule that undoes it
  • The November withholding check-up
  • Washington capital gains planning before year end

December

  • The year-end checklist, in the order things expire
  • Preparing for 1099 season in December, not January
  • Charitable giving: timing, bunching and what actually helps
  • Planning a cross-border move for January

Planned posts deliberately have no URL until they are written. Publishing forty-two empty stubs would recreate the exact thin-content problem this site was rebuilt to fix.

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