Why the quarters aren't evenly spaced
Notice that "Q2" only covers two months (April–May) and "Q4" covers four (September–December). The IRS's quarterly system isn't really four equal three-month blocks — it's four payment deadlines spread across the year at roughly these intervals, inherited from a calendar that predates modern payroll withholding. Just memorize the four dates: April 15, June 15, September 15, and January 15 (of the following year).
What if a due date falls on a weekend or holiday?
If any of these dates falls on a Saturday, Sunday, or federal legal holiday, the deadline shifts to the next business day. Always double-check the exact date on the current year's IRS Form 1040-ES page before paying, since state and local holidays can occasionally shift a due date too.
The safe-harbor rule: how to avoid an underpayment penalty
Generally, you can avoid the IRS underpayment penalty if you pay, through withholding and timely estimated payments combined, at least the smaller of:
- 90% of the tax you'll owe for the current year (2026), or
- 100% of the tax you owed last year (2025) — or 110% of last year's tax if your 2025 adjusted gross income was above $150,000 ($75,000 if married filing separately).
The second option is often the easiest for freelancers with irregular income: if you know last year's total tax bill, you can divide it by four and pay that amount each quarter, regardless of how this year's income actually comes in, and stay penalty-safe.
How to pay
Estimated payments can be made online via IRS Direct Pay, the Electronic Federal Tax Payment System (EFTPS), by debit/credit card through an IRS-approved processor, or by mailing a check with Form 1040-ES. Keep the confirmation number or mailed receipt — you'll want it if a payment ever gets questioned.
Sources
- IRS — Form 1040-ES, Estimated Tax for Individuals (2026 due dates)
- IRS — Underpayment of Estimated Tax by Individuals Penalty (safe-harbor rule)