
Hi, I'm Slava, CEO and co-founder of Jupid. After helping 60,000+ small business owners at Anna Money and now building Jupid, I've watched countless entrepreneurs get blindsided by their first quarterly tax bill. The IRS expects you to pay as you earn—not just once a year—and missing payments leads to penalties that add up fast.
If you're self-employed, a freelancer, or have significant income without withholding, quarterly estimated taxes aren't optional. Form 1040-ES is how you calculate and pay them. This guide walks you through every deadline, calculation, and strategy to stay compliant without overpaying.
Estimated taxes are periodic payments you make to the IRS throughout the year on income that doesn't have taxes withheld. While W-2 employees have taxes automatically deducted from each paycheck, self-employed individuals must calculate and pay their own taxes quarterly.
Legal Basis: IRC §6654 requires individuals to pay estimated tax if they expect to owe $1,000 or more when filing their return.
The US tax system operates on a "pay-as-you-go" basis. You're supposed to pay taxes on income as you earn it, not wait until April of the following year. For employees, employers handle this through withholding. For the self-employed, you handle it yourself using Form 1040-ES.
Form 1040-ES (Estimated Tax for Individuals) is the IRS form that helps you:
| Item | 2026 Details |
|---|---|
| Threshold to Pay | Expect to owe $1,000+ after withholding |
| Q1 Deadline | April 15, 2026 |
| Q2 Deadline | June 16, 2026 |
| Q3 Deadline | September 15, 2026 |
| Q4 Deadline | January 15, 2027 |
| Safe Harbor (Under $150K AGI) | Pay 100% of prior year tax |
| Safe Harbor ($150K+ AGI) | Pay 110% of prior year tax |
| Penalty Rate | IRS interest rate (currently ~8% annually) |
Legal Basis: IRC §6654, IRS Publication 505 (Tax Withholding and Estimated Tax)
You generally must make estimated tax payments if both of these apply:
✅ Self-employed (sole proprietor, freelancer, independent contractor) ✅ Single-member LLC owner ✅ Partner in a partnership ✅ S Corporation shareholder (for your share of pass-through income) ✅ Receiving significant income without withholding (investments, rental income) ✅ Gig worker (Uber, DoorDash, Etsy seller, etc.)
❌ You expect to owe less than $1,000 in tax ❌ You had no tax liability last year AND were a US citizen/resident for the full year ❌ Your employer withholds enough from your W-2 to cover all taxes
Pro tip: If you have a W-2 job plus self-employment income, you can often increase your W-2 withholding to cover your self-employment tax, avoiding quarterly payments entirely.
Estimated taxes are due four times per year. Despite being called "quarterly," the periods aren't equal—Q2 is only two months.

| Payment Period | Income Earned | Due Date |
|---|---|---|
| Q1 | January 1 – March 31 | April 15, 2026 |
| Q2 | April 1 – May 31 | June 16, 2026 |
| Q3 | June 1 – August 31 | September 15, 2026 |
| Q4 | September 1 – December 31 | January 15, 2027 |
Important: If a deadline falls on a weekend or federal holiday, the due date moves to the next business day.
Exception: If you file your tax return and pay all tax owed by January 31, 2027, you can skip the Q4 estimated payment.
Form 1040-ES includes a worksheet that walks you through the calculation. Here's the process simplified:
Start with expected income from all sources:
Subtract adjustments to income:
From your AGI, subtract:
Apply the 2026 tax brackets to your taxable income:
2026 Tax Brackets (Single)
| Taxable Income | Tax Rate |
|---|---|
| $0 – $11,925 | 10% |
| $11,926 – $48,475 | 12% |
| $48,476 – $103,350 | 22% |
| $103,351 – $197,300 | 24% |
| $197,301 – $250,525 | 32% |
| $250,526 – $626,350 | 35% |
| Over $626,350 | 37% |
Add self-employment tax:
See our Schedule SE Instructions Guide 2026 for detailed self-employment tax calculations.
Subtract:
The result is your required annual payment. Divide by 4 for quarterly payments (or allocate based on when income is earned).
Scenario: Sarah, a freelance designer
Estimated self-employment income: $120,000
Standard deduction: -$15,000
QBI deduction (20%): -$21,000
Taxable income: $84,000
Federal income tax: ~$13,500
Self-employment tax: ~$17,000
Total tax: ~$30,500
Credits and withholding: $0
Required annual payment: $30,500
Quarterly payment: $7,625
The IRS won't penalize you for underpayment if you meet one of these "safe harbor" thresholds:
Pay at least 90% of your current year tax liability through estimated payments and withholding.
Risk: If your income is higher than expected, you'll owe at tax time (possibly with penalties).
Pay 100% of your prior year's total tax liability. If your prior year AGI exceeded $150,000 ($75,000 if married filing separately), pay 110% instead.
Advantage: You know exactly how much to pay—it's right on last year's return. No guessing about future income.
| Situation | Best Safe Harbor |
|---|---|
| Income similar to last year | Either works |
| Income increasing significantly | Prior year (100%/110%) |
| Income decreasing significantly | Current year (90%) |
| Unpredictable income | Prior year (safest) |
| First year self-employed | Estimate conservatively |
Example:
Last year's total tax: $25,000
This year's expected tax: $35,000
Prior year AGI: $200,000 (over $150K threshold)
Prior year safe harbor: $25,000 × 110% = $27,500
Quarterly payment: $27,500 ÷ 4 = $6,875
Result: Pay $6,875/quarter to avoid penalties,
even if you owe $7,500 at tax time
The fastest, free way to pay:
Advantage: Immediate confirmation, no fees, no registration required.
For recurring scheduled payments:
Advantage: Schedule all four payments at once. Set it and forget it.
Pay from your phone using the IRS2Go app (available on iOS and Android). Same process as Direct Pay, mobile-friendly interface.
Pay through IRS-approved payment processors. Fees apply:
When this makes sense: If you need to float payment timing or earn significant credit card rewards.
Include a payment voucher from Form 1040-ES with a check or money order. Mail to the address listed in the form instructions for your state.
Mailing addresses vary by state. Check Form 1040-ES Instructions for your specific address.
Tip: Mail early. The IRS uses the postmark date, but delays happen.
The IRS charges interest on underpaid estimated taxes. The penalty is calculated separately for each quarter based on:
Annualized Income Installment Method: If your income varies significantly throughout the year, you can use Form 2210 to calculate penalties based on when you actually earned income. This helps if you earned most income later in the year.
Example: You earned $10,000 in Q1 but $40,000 in Q4. The annualized method may reduce or eliminate penalties even if you paid less earlier.
The IRS may waive penalties if:
No prior year tax to base safe harbor on? Use the current year 90% method, but estimate conservatively. Better to overpay and get a refund than underpay and owe penalties.
Strategy: Take your expected annual income, calculate taxes, add 10-15% buffer, divide by 4.
You have options:
Pro tip: Increasing W-2 withholding is treated as paid evenly throughout the year, even if done late. Estimated payments apply only to the quarter paid.
If income fluctuates significantly:
If your S Corp pays you a reasonable salary, taxes are withheld from that salary. You may still need estimated payments for:
Many new freelancers calculate income tax but forget that self-employment income also incurs an additional 15.3% SE tax. This can nearly double your expected tax bill.
Solution: Always include SE tax in your calculations. Use our Self-Employment Tax Calculator to estimate your total liability.
Your income may change year to year. Blindly paying last year's amount could leave you owing a large balance (or overpaying significantly).
Solution: Review your current year income quarterly. Adjust payments if income is significantly different.
Estimated tax deadlines are firm. Late payments incur penalties from the due date, not your payment date.
Solution: Set calendar reminders. Better yet, use EFTPS to schedule all four payments at the beginning of the year.
Q4 covers September through December—often the highest-income months for many businesses. Paying the same amount as Q1-Q3 may leave you short.
Solution: If using the 90% current year method, recalculate in Q4 based on actual year-to-date income.
If you have sufficient W-2 withholding, you may not need to make estimated payments at all.
Solution: Check if you'll owe $1,000+ after withholding. If not, estimated payments are optional.
The Form 1040-ES includes a detailed worksheet. Here's a simplified version:
Your total expected income minus adjustments (self-employed health insurance, half of SE tax, retirement contributions).
Subtract your standard deduction (or itemized deductions) and QBI deduction.
Line 1 minus Lines 2-3.
Apply tax rates to Line 4, add self-employment tax and other taxes.
Subtract expected credits (child tax credit, education credits, etc.).
Add other taxes (alternative minimum tax, if applicable).
Your expected total tax liability.
Calculate required annual payment based on safe harbor rules.
Divide Line 14 by 4. This is your quarterly estimated payment.
Calculating estimated taxes requires tracking income throughout the year, understanding safe harbor rules, and remembering quarterly deadlines. Miss a payment or miscalculate, and you're facing IRS penalties.
What makes Jupid different:
✅ Real-time tax projection — Know your estimated tax liability as income comes in, not just at quarter-end
✅ Automatic payment reminders — Never miss a deadline with timely notifications
✅ Safe harbor calculations — We automatically calculate both safe harbor options and recommend the best approach
✅ Quarterly reconciliation — Adjust payments mid-year as your income changes
✅ Chat with your AI accountant — Ask questions like "How much should I pay in Q3?" and get instant, personalized answers
Example conversation:
Stop guessing about quarterly payments. Let Jupid handle the calculations while you focus on your business.
Estimated taxes are a pay-as-you-go obligation that catches many self-employed individuals off guard. The key principles:
The goal isn't to pay the exact right amount—it's to pay enough to avoid penalties while not overpaying significantly. When in doubt, err on the side of paying slightly more. You'll get it back as a refund.
Disclaimer
This article provides general information about tax payments and should not be considered tax advice. Tax laws change frequently, and individual circumstances vary significantly. For advice specific to your situation, consult with a qualified tax professional.
Tax Year: 2026 Last Updated: January 27, 2026
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