Estimated Tax Deadlines 2026: Dates, Safe Harbor, and Penalties
If you are self-employed, freelance, or under-withheld, the IRS expects you to pay tax as you earn — in four quarterly installments. Missing one is expensive, and the dates are not evenly spaced. Here are the 2026 deadlines and the rules that decide whether you owe a penalty.
The four 2026 due dates
| Quarter | Income earned | Payment due |
|---|---|---|
| 1 | January 1 – March 31 | April 15, 2026 |
| 2 | April 1 – May 31 | June 15, 2026 |
| 3 | June 1 – August 31 | September 15, 2026 |
| 4 | September 1 – December 31 | January 15, 2027 |
Notice quarter 2 covers only two months and quarter 4 covers four — the IRS sets the dates this way so the payments roughly match when income arrives.
Who must make estimated payments
You generally must pay estimated tax if you expect to owe at least $1,000 for the year after withholding and credits — the classic cases being self-employment income, rental or investment income without withholding, or a W-2 job where too little is withheld. If most of your income is withheld from a paycheck and you owe less than $1,000, you are usually fine without them.
Safe harbor: the two ways to avoid the penalty
You avoid the underpayment penalty if your payments and withholding cover either: (1) 90% of this year’s total tax, or (2) 100% of last year’s total tax (110% if your prior-year adjusted gross income was over $150,000). The second rule is the one most people rely on: if your income spiked this year, paying the same amount as last year keeps you penalty-free — you settle the difference when you file.
What the penalty actually costs
Underpayment is charged interest on what you should have paid, computed from each payment’s due date to the date you paid — the current underpayment rate is set quarterly and applies even if your return shows a refund. If your income arrived unevenly during the year, the annualized income installment method on Form 2210 can reduce or eliminate the penalty, but it requires the paperwork to prove the timing.
Run the numbers
Use the estimated quarterly tax calculator to size each of your four payments from your profit and filing status, and check your self-employment tax with the self-employment tax calculator. See the full-year picture with the federal income tax calculator — and if your W-2 job is under-withholding, fix it with the withholding calculator. Everything you can deduct while paying is in the 2026 tax deductions guide.