The Four Quarterly Due Dates for 2025

Despite the name “quarterly,” the four payment periods aren’t evenly spaced. The first two are only two months apart. Here are the 2025 deadlines (per IRS Form 1040-ES instructions):

• Q1 — April 15, 2025: Covers income earned January 1 through March 31
• Q2 — June 16, 2025: Covers income earned April 1 through May 31 (yes, just two months)
• Q3 — September 15, 2025: Covers income earned June 1 through August 31
• Q4 — January 15, 2026: Covers income earned September 1 through December 31

June 15 falls on a Sunday in 2025, so the Q2 deadline shifts to Monday, June 16. All other dates land on weekdays and stand as listed.

The Q4 payment is technically for 2025 income, but it’s not due until January 15 of the following year. If you file your 2025 tax return and pay any remaining balance by February 1, 2026, you can skip the Q4 estimated payment entirely — but that’s a tight turnaround. Most people just pay the estimate in January.

Who Needs to Make Estimated Payments

The general rule per IRC §6654: if you expect to owe $1,000 or more in federal tax after subtracting withholding and credits, you need to make estimated payments. That catches a lot of people who don’t think of themselves as “quarterly filers.”

The obvious group is self-employed individuals — freelancers, consultants, sole proprietors, single-member LLC owners. You have no employer withholding taxes for you, so estimated payments are your substitute.

But plenty of W-2 employees need to pay quarterly too. If you have significant investment income (dividends, capital gains, interest), rental income, or a side business, your W-2 withholding probably doesn’t cover the full tax on everything. A teacher who earns $30,000 in rental income on the side isn’t going to have tax withheld on those rents unless they adjust their W-4.

Retirees with pension income and Social Security benefits sometimes need estimated payments if their withholding elections don’t cover the tax. Partners and S-corp shareholders receiving K-1 income almost always do.

High-income W-2 earners are another group that gets caught. If you earn $400,000 in salary and your withholding is set to cover that amount, but you also realize $100,000 in capital gains from stock sales, the withholding won’t cover the gains. The IRS doesn’t care that you didn’t know about the gains until December — they want quarterly payments.

The Safe Harbor Rules: How to Avoid Penalties

You won’t owe an underpayment penalty if your estimated payments (plus any withholding) meet one of these two tests (per IRC §6654(d)):

• 90% of current-year tax: Your total payments cover at least 90% of the tax shown on your 2025 return.
• 100% of prior-year tax: Your total payments equal at least 100% of the tax shown on your 2024 return. This jumps to 110% if your 2024 adjusted gross income exceeded $150,000 ($75,000 if married filing separately).

The prior-year safe harbor is the one most people rely on. If you owed $30,000 in federal tax for 2024 and your AGI was over $150,000, you need to pay at least $33,000 (110%) in estimated payments and withholding during 2025 to avoid penalties. Even if your actual 2025 tax turns out to be $50,000, you won’t owe an underpayment penalty as long as you hit the $33,000 threshold.

This is the most common planning strategy for people with unpredictable income. You can’t know in April what your capital gains will be in October. But you can look at last year’s return, calculate 110%, divide by four, and send those payments. Anything else you owe gets settled at filing time — penalty-free.

How to Calculate Your Estimated Tax Using Form 1040-ES

The IRS publishes Form 1040-ES with a worksheet for calculating estimated payments. The basic process:

Start with your expected adjusted gross income for 2025. Subtract your expected deductions (standard or itemized). That gives you estimated taxable income. Apply the tax brackets. Add self-employment tax if applicable. Subtract expected credits (child tax credit, education credits, etc.). The result is your estimated total tax.

Now subtract any withholding you expect from W-2 jobs or other sources. The remaining amount is what you owe in estimated payments. Divide by four for equal quarterly installments.

The worksheet is straightforward for people with stable income. For freelancers whose income swings wildly from quarter to quarter, the worksheet can feel like guessing. If that’s you, the prior-year safe harbor is your friend — or consider the annualized income installment method, which we’ll cover below.

How to Pay: EFTPS, Direct Pay, and Other Options

You’ve got several ways to send estimated tax payments to the IRS:

• IRS Direct Pay (irs.gov/payments): Free. Pay directly from your bank account. No registration required. Select “Estimated Tax” and the correct tax year. You get immediate confirmation.
• EFTPS (Electronic Federal Tax Payment System): Free. Requires enrollment (takes about a week to set up). Allows scheduling payments in advance. This is what most businesses use, and it works for individuals too.
• Credit or debit card: You can pay through IRS-approved processors, but they charge a fee — typically 1.85% to 1.98% for credit cards or a flat fee around $2.50 for debit cards. Only makes sense if you’re earning rewards that exceed the fee.
• Check or money order: Mail to the IRS with a 1040-ES voucher. Slow, no confirmation until your check clears, and the IRS can lose mail. We don’t recommend this unless you have no other option.

For most people, IRS Direct Pay is the simplest choice. You can even set it up the morning a payment is due and still make the deadline.

State Estimated Taxes: Don’t Forget Those

Federal estimated payments are only half the picture. Most states with an income tax have their own quarterly estimated tax requirements with their own due dates, which don’t always match the federal schedule.

New York: NYS estimated tax due dates generally follow the federal schedule (April 15, June 15, September 15, January 15). Pay through the NYS Tax Department website. If you live in NYC, your state estimated payment covers both NYS and NYC income tax — there’s no separate city payment.

California: California uses a different payment schedule: 30% due April 15, 40% due June 16, 0% due September 15 (yes, zero), and 30% due January 15. This trips up California taxpayers who assume it mirrors the federal 25/25/25/25 split. Pay through the FTB website.

Florida, Texas, Nevada, Wyoming, and other no-income-tax states: No state estimated payments required. One less thing to track.

If you live in one state and work in another, you may owe estimated payments to both. Remote work has made this even more complicated since 2020.

What Happens If You Underpay

The underpayment penalty is calculated on Form 2210 and works like interest on the amount you should have paid but didn’t. It’s not a flat penalty — it’s applied quarter by quarter based on the federal short-term interest rate plus 3 percentage points. For 2025, that rate is around 7-8%, which makes underpayment penalties more expensive than they’ve been in years.

The penalty applies even if you get a refund. You could owe $40,000 total, make no estimated payments all year, then pay $45,000 when you file and get a $5,000 refund — and still owe an underpayment penalty on each quarter where your cumulative payments were short.

The IRS calculates the penalty automatically when you file, or you can calculate it yourself on Form 2210. Some people choose to accept the penalty intentionally, treating it as the cost of borrowing from the government. At 7-8%, that’s not cheap money, but it’s better than the interest on some credit cards.

The Annualized Income Installment Method

If your income is heavily concentrated in one part of the year — maybe you’re a real estate agent who closes most deals in Q2 and Q3, or a freelancer who lands a big contract in October — the standard equal-payment approach can create penalties for quarters where you genuinely had little income.

The annualized income installment method (Schedule AI of Form 2210) lets you calculate each quarter’s required payment based on the income you actually earned through the end of that quarter, annualized. If you earned almost nothing in Q1, your required Q1 payment is small — even if your total annual income ends up being $300,000.

The math is tedious. You’re essentially preparing four partial-year tax calculations. Most tax software handles it automatically once you indicate you want to use the annualized method. It’s worth the effort for anyone whose income is genuinely uneven across quarters. For freelancers with steady monthly income, the standard method is simpler and works fine.

An Alternative: Adjust Your W-4 Withholding

If you have a W-2 job in addition to self-employment or investment income, there’s a simpler approach than writing four quarterly checks. Increase your W-4 withholding to cover the extra tax. The IRS treats W-2 withholding as paid evenly throughout the year, even if you increase it in December. That’s an advantage over estimated payments, which are assigned to specific quarters.

Here’s what that looks like in practice: you realize in November that you owe $20,000 more than you’ve paid so far. If you send that as a Q4 estimated payment, the IRS could still penalize you for underpaying Q1 through Q3. But if you ask your employer to withhold an extra $20,000 from your remaining paychecks, the IRS treats it as if $5,000 was withheld in each quarter. No underpayment penalty.

This only works if you have W-2 income. And your employer has to be willing to process the increased withholding quickly. But it’s a legitimate — and often overlooked — way to fix a late-year estimated tax shortfall. Talk to your tax preparer about whether it makes sense for your situation.

Sources & References

• IRS Form 1040-ES — Estimated Tax for Individuals
• IRC §6654 — Failure by Individual to Pay Estimated Income Tax (Cornell Law)
• IRS Direct Pay — Pay Your Tax Bill Directly From Your Bank Account
• EFTPS — Electronic Federal Tax Payment System
• IRS Form 2210 — Underpayment of Estimated Tax by Individuals
• New York State — Estimated Tax Payments
• California FTB — Estimated Tax Payments