One of the most jarring transitions for new business owners is the shift from being an employee to being an employer—or simply being self-employed. When you work a traditional 9-to-5 job, your taxes are quietly withheld from every paycheck. You rarely think about them until you file your annual return.
As a business owner, that safety net is gone. The U.S. operates on a “pay-as-you-go” tax system. The IRS expects to receive tax payments on your income as you earn it throughout the year, not just once at the end. This means that for most entrepreneurs, tax day isn’t just in April; it happens four times a year.
Missing these quarterly deadlines is one of the most common ways small businesses incur unnecessary penalties. It can also lead to a cash flow crisis when a massive, unexpected tax bill comes due all at once.
In this guide, we’ll break down the essential 2025 quarterly tax deadlines, explain who needs to pay, and show you how to calculate what you owe so you can stay compliant and stress-free.
For a complete overview of all tax obligations this year, be sure to bookmark our 2025 Small Business Tax Season Toolkit.
The 2025 Estimated Tax Payment Schedule
If you owe at least $1,000 in taxes for the year (after subtracting your withholding and refundable credits), you generally must make estimated tax payments. This applies to sole proprietors, partners, and S-corporation shareholders.
Mark these dates on your calendar immediately. Note that, unlike standard calendar quarters, the IRS payment periods are not perfectly spaced.
Quarter 1 (Payment Period: Jan 1 – March 31)
- Deadline: April 15, 2025
- Note: This coincides with the annual filing deadline for the previous tax year. It’s a “double-whammy” day where you pay any remaining balance for 2024 and your first installment for 2025.
Quarter 2 (Payment Period: April 1 – May 31)
- Deadline: June 16, 2025
- Note: This is often the deadline that catches owners off guard because it comes just two months after the Q1 deadline. Since June 15 falls on a Sunday in 2025, the deadline moves to the next business day.
Quarter 3 (Payment Period: June 1 – Aug 31)
- Deadline: September 15, 2025
- Note: This payment covers the summer months. It’s crucial not to let vacation spending deplete the cash reserves you need for this payment.
Quarter 4 (Payment Period: Sept 1 – Dec 31)
- Deadline: January 15, 2026
- Note: This final payment wraps up the 2025 tax year. While it isn’t due until the new year begins, it counts toward your 2025 tax liability.
Payroll Tax Deadlines (Form 941)
If you have employees, you have additional quarterly responsibilities. You must withhold federal income tax, Social Security, and Medicare taxes from your employees’ paychecks and remit them to the IRS.
You report these amounts quarterly using Form 941, Employer’s Quarterly Federal Tax Return.
- Q1 Filing Deadline: April 30, 2025
- Q2 Filing Deadline: July 31, 2025
- Q3 Filing Deadline: October 31, 2025
- Q4 Filing Deadline: January 31, 2026
Tip: If you have deposited all taxes on time and in full, you have an additional 10 days (until the 10th of the following month) to file Form 941.
Who Needs to Pay Quarterly Estimated Taxes?
The general rule is simple: If you expect to owe $1,000 or more in tax when you file your return, you need to make estimated payments.
This typically affects:
- Sole Proprietors & Freelancers: Since no taxes are withheld from client payments.
- Partners & S-Corp Shareholders: You pay taxes on your share of the business profits at your individual income tax rate.
- Landlords: Rental income is taxable and not subject to withholding.
- Gig Workers: Uber drivers, DoorDashers, and other platform workers.
Corporations usually have to make estimated tax payments if they expect to owe tax of $500 or more for the tax year.
How to Calculate Your Payments
Calculating estimated taxes can feel like predicting the future, especially if your business income fluctuates. However, the IRS offers two methods to help you avoid penalties.
Method 1: The “Safe Harbor” Rule (Easiest)
To avoid an underpayment penalty, you generally need to pay at least:
- 90% of the tax you will owe for the current year (2025), OR
- 100% of the tax you owed for the prior year (2024).
Note: If your adjusted gross income for 2024 was over $150,000 ($75,000 if married filing separately), you must pay 110% of your 2024 tax.
Using the 100% (or 110%) prior-year rule is the safest and easiest method. Simply take your total tax from your 2024 return, divide it by four, and pay that amount each quarter. You might still owe more (or get a refund) when you file, but you won’t face penalties for underpayment.
Method 2: Annualized Income Installment Method (Most Accurate)
If your business is seasonal—for example, a landscaping company that makes 80% of its revenue in summer—paying equal quarterly installments might hurt your cash flow in the winter.
Using the annualized method, you calculate your tax liability at the end of each quarter based on what you actually earned up to that point. This requires meticulous bookkeeping and filing Form 2210 with your tax return, but it aligns your tax payments with your cash flow.
The Cost of Missing a Deadline
The IRS imposes an underpayment penalty if you don’t pay enough tax throughout the year. This functions like interest on a loan. The penalty rate is determined quarterly and applies to the amount you failed to pay.
Even if you file your annual return on time and pay the remaining balance in April, you can still be penalized if you skipped the quarterly payments earlier in the year. The IRS effectively says, “You owed us this money in June, not next April.”
How to Stay on Track
Managing quarterly taxes requires organization and discipline. Here are three tips to ensure you never miss a deadline:
- The 30% Rule: A good rule of thumb is to set aside 25-30% of every payment you receive into a separate business savings account. Label this account “Taxes – Do Not Touch.” When the quarterly deadline arrives, the money is already there.
- Leverage Your Bookkeeping: You cannot calculate accurate tax payments if you don’t know your profit. Up-to-date bookkeeping is essential. If your books are months behind, you are essentially guessing at your tax liability.
- Automate Reminders: Set calendar alerts for one week before each deadline. This gives you time to transfer funds and process the payment via the IRS Direct Pay system or EFTPS.
Conclusion
Quarterly taxes are a reality of running a successful business. While they require extra administrative work, they also serve as a regular check-in on your financial health. By understanding the 2025 schedule and planning your cash flow accordingly, you can turn tax deadlines from a source of panic into just another routine business task.
If calculating these payments feels overwhelming, or if your books aren’t ready to give you the numbers you need, it might be time to bring in support. Professional bookkeeping ensures you always have the accurate data required to make precise payments.
Ready to master the rest of the tax year? Head over to our 2025 Small Business Tax Season Toolkit for more guides on deductions, credits, and filing strategies.