Quarterly Tax Deadlines: 2026 & 2027

Who has to make quarterly payments?

The IRS expects tax to be paid as income is earned. If you expect to owe at least $1,000 when you file — which happens fast once freelance profit passes roughly $5,000 — you're generally required to send estimated payments four times a year using Form 1040-ES. Employees avoid this because their employer withholds from every paycheck.

Note that the quarters aren't equal: the second "quarter" covers only April and May, while the fourth covers four months. That quirk catches people who assume payments land every three months.

How much should each payment be?

The safest approach is the IRS safe harbor: pay at least 90% of what you'll owe this year, or 100% of what you owed last year (110% if your prior-year adjusted gross income topped $150,000). Meet either target and you avoid the underpayment penalty even if you end up owing more at filing. Our quarterly tax calculator estimates the amount from your expected profit; for a fuller picture use the all-in-one freelancer tax calculator. Next up: September 15, 2026 (Q3).

How to pay

IRS Direct Pay moves money straight from your bank account with no fee and gives you a confirmation number — it's the fastest option for most freelancers. You can also pay through your IRS Online Account, by card for a processing fee, or by mailing a check with a 1040-ES voucher. If your state has an income tax, it almost certainly wants its own estimated payments on a similar schedule through its own portal.

The date is not the 1099 amount

A 1099-NEC or 1099-K does not tell you what to send on September 15. The slip is a year-end information return; estimated tax is a running prepayment on profit. Start with the 1099 tax calculator hub for the SE slice, then the self-employment tax calculator if you only need Schedule SE, then come back here for the calendar. First year on 1099? Read first 1099 taxes before you skip Q3 because “the form hasn’t arrived yet.”

Worked catch-up: you underpaid Q1 and Q2

Same $73,000 Single 1099 profit as the flagship SE calculator (default $85,000 − $12,000). Dollars come from seTaxCalc and federalSetAside in assets/app.js — rounded the way those tools display. This is not a Form 2210 penalty quote; it is the equal-installment math those pages already use.

Safe harbor can still wipe the penalty even if this year’s tax is higher — 90% of this year, or 100% of last year (110% if prior-year AGI was over $150,000). First-year filers with little prior-year tax should still move cash; April is a cliff even when the penalty rule is softer. Catch-up dollars are three-quarters of the unrounded annual, then rounded (they can differ by $1 from 3 × the displayed quarter). Line-by-line SE math: three worked examples. Penalty worksheet: Form 2210 calculator.

Frequently asked questions