Quarterly estimated taxes for federal, Oregon and Portland

Who needs to make quarterly estimated taxes

The IRS says individuals, including sole proprietors, partners and S corporation shareholders, generally have to make estimated payments if they expect to owe $1,000 or more when their return is filed. Corporations generally have to pay estimates if they expect to owe $500 or more. Estimated tax covers more than income tax. It also pays self employment tax, which is often the bigger surprise for people in their first year of freelancing.

In practice that means most self employed people, most landlords with profitable rentals, and anyone with large investment income or stock sales. It also catches employees whose withholding falls short, such as tech workers in Hillsboro and Beaverton whose RSUs vest without enough tax withheld to cover the real bill.

Tell us what you need and a licensed CPA who works with people like you gets in touch with a clear, fixed quote.

Federal Form 1040-ES due dates for tax year 2026

Federal estimates for tax year 2026 are due on 4/15/2026, 6/15/2026, 9/15/2026 and 1/15/2027, according to the IRS Taxpayer Advocate Service calendar. You make them with Form 1040-ES or online through your IRS account, Direct Pay, or the IRS app. Businesses can also pay through their business tax account, and some business payments still go through EFTPS, the Electronic Federal Tax Payment System.

The four payments are not evenly spaced. The second one comes only two months after the first, and the last one lands after the year has ended. People who set up a calendar reminder for every three months often miss the June payment.

If your income is lumpy, equal payments may not be the best fit. A CPA can look at when you actually earn the money and plan payments around it, which helps contractors with a busy summer or consultants paid on big projects.

How to avoid the federal underpayment penalty

The IRS says most taxpayers avoid the underpayment penalty if they owe less than $1,000 after withholding and credits. Otherwise, you generally avoid it by paying the smaller of 90% of this year's tax or 100% of the tax shown on last year's return. Special rules apply to farmers, fishermen and certain higher income taxpayers, which IRS Publication 505 explains.

That prior year option is useful when your income is rising, because it gives you a fixed target you can plan around. The catch is that you still owe the full balance when you file, so a CPA will usually also estimate the real bill and help you save for it.

Oregon estimated tax payments

The Oregon Department of Revenue says you must make estimated payments if you expect to owe $1,000 or more after all credits and withholding. For tax year 2025, the Oregon installments were due on 4/15/2025, 6/16/2025, 9/15/2025 and 1/15/2026, the same days as the federal payments that year.

You can pay from a checking or savings account through Revenue Online, and card payments may carry a convenience fee. Form OR-40-V is only for payments sent by check or money order.

Oregon has its own safe harbor. For tax year 2025, the required annual payment was the lesser of 90% of your 2025 tax after credits or 100% of the tax after credits on your 2024 return, and to use the prior year option you had to file your 2024 return before your 2025 return. Underpayment interest is charged on each short installment until it is paid or the return is due.

Portland local estimates: Metro SHS, Preschool for All and business taxes

Higher earners in the Portland area can also owe quarterly payments to the City of Portland Revenue Division for the Metro Supportive Housing Services and Multnomah County Preschool for All personal income taxes. Through tax year 2025, estimates were required for a program when both the current year and prior year liability for that program were $1,000 or more. The Revenue Division lists a $5,000 trigger starting with tax year 2026.

Each local payment must be at least 25% of the current year's estimated liability. Personal payments are due on 4/15, 6/15, 9/15 and 1/15. You avoid quarterly underpayment interest if you paid at least 90% of the current year's liability or 100% of the prior year's liability by the 1/15 payment.

Businesses that file the combined City of Portland and Multnomah County business tax return follow a slightly different calendar. For calendar year filers, local business estimates are due on 4/15, 6/15, 9/15 and 12/15, with underpayment interest of 10% a year on late or short payments. Larger companies paying the Oregon Corporate Activity Tax have yet another schedule, with calendar year payments due 4/30, 7/31, 10/31 and 1/31.

How a CPA sets up your estimates

The CPA you are matched with will start with last year's federal, Oregon and local returns, then look at what you have earned so far and what is coming. They will tell you how much to send to the IRS, the Oregon Department of Revenue and, if it applies, the City of Portland, and on which dates.

Many clients check in once or twice during the year, often after a big contract, an RSU vest or a property sale, so the remaining payments can be adjusted. That small amount of attention tends to be cheaper than a penalty, and far less stressful than a large balance due on 4/15.

Common questions