The U.S. tax system is pay-as-you-go, which means waiting until April to pay what you owe could result in an estimated tax penalty. This can come as a surprise for self-employed individuals and business owners who are used to handling their taxes once a year.
For freelancers and gig workers especially, understanding estimated payments can help you stay ahead of your tax obligations throughout the year. See our guide to filing taxes for freelancers and gig workers to learn more about managing your taxes as a self-employed worker.
Who Actually Has to Pay Quarterly
Individuals generally need to make quarterly estimated tax payments if they expect to owe $1,000 or more in taxes when they file. This commonly applies to freelancers, independent contractors, landlords, and S corp owners who take distributions because taxes may not automatically be withheld from their income. You may also need to make quarterly payments if you earn income from a side business or other source and your regular withholding isn’t enough to cover your total tax liability.
When Are Quarterly Taxes Due in 2026?
Estimated tax payments are generally made four times throughout the year. For 2026, the payment schedule is:
- April 15, 2026
- June 15, 2026
- September 15, 2026
- January 15, 2027
If you’re unsure how to pay quarterly taxes, you can make your payments online through IRS Direct Pay or your IRS Online Account.
The Estimated Tax Penalty (and the Safe Harbor That Avoids It)
The estimated tax penalty is interest-based and calculated using the IRS underpayment rate, which is currently 7% for Q3 2026 and adjusted quarterly. If you miss an estimated payment, making it as soon as possible can help prevent additional interest and penalties from continuing to accrue.
One way to avoid the penalty is through the safe harbor rule. Generally, you can qualify by paying at least 90% of your current year’s tax or 100% of the previous year’s tax, whichever is smaller. For higher earners with an AGI over $150,000, the prior-year threshold increases to 110%.
In practice, safe harbor can mean looking at your total tax from the previous year and using that amount to calculate your estimated payments throughout the year. Staying consistent with these payments can help you avoid falling behind, especially if you’re self-employed and don’t have taxes automatically withheld from each paycheck.
Get Ahead of September 15
With the third-quarter estimated tax payment due September 15. Taking 20 minutes to review your tax situation now can help you avoid an unexpected penalty letter in the spring. Boxelder’s accounting and bookkeeping team can help you stay on top of your tax obligations and prevent problems before they start. We help you resolve tax debt and avoid creating it in the first place. Review our individual tax checklist or contact our team to get started.
Disclaimer: This content is for informational purposes only and should not be considered tax, legal, or financial advice. Every tax situation is different. Consult a qualified tax professional regarding your specific circumstances.
