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Learn everything you need to know about quarterly estimated taxes due June 15—who must pay, how to calculate what you owe, common mistakes to avoid, and how to stay compliant with the IRS.
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If you're self-employed, a freelancer, an investor, or a small business owner, June 15 is one of the most important tax deadlines of the year. That’s because it’s the due date for the second installment of quarterly estimated taxes. Missing it can lead to unnecessary penalties, interest, and IRS stress.
In this comprehensive guide, we’ll break down what estimated taxes are, who needs to pay them, how to calculate what you owe, and strategies for staying organized and compliant—especially with the second-quarter deadline fast approaching.
The IRS operates on a “pay-as-you-go” tax system. That means taxes on income must be paid throughout the year as you earn it—not just in April.
When you’re an employee, your employer withholds federal income tax from your paychecks. But if you’re self-employed or earn other income without withholdings (like from investments, rental properties, or side gigs), you’re responsible for making estimated tax payments each quarter.
There are four estimated tax payment deadlines every year:
These deadlines fall around the 15th of the month following each quarter, except for Q4.
Not everyone is required to make estimated payments. However, you must pay them if both of the following apply:
1) You expect to owe at least $1,000 in tax for the year after subtracting withholding and refundable credits.
2) Your withholding and credits will be less than the smaller of:
You’ll likely need to make estimated payments if you:
The goal is to avoid underpaying (which leads to penalties) and overpaying (which gives the government an interest-free loan). Here are a few options to calculate your payment:
This is the easiest way to avoid penalties. Pay:
✅ This works well if your income is relatively stable.
If your income varies throughout the year (e.g., seasonal business), you can calculate each quarter’s payment based on your actual income for that period using IRS Form 2210.
Estimate your full-year income and deductions, then calculate your tax liability as if it were year-end. Divide this by four and pay that amount quarterly.
💡 Use IRS Form 1040-ES to calculate your payments and get vouchers for mailing.
You can pay estimated taxes in several ways:
Keep confirmation numbers and receipts. These can come in handy during tax prep season or in the event of a dispute.
Even if you’re only a few days late, the IRS may charge interest and penalties. Mark June 15 clearly in your calendar!
Using incorrect income estimates or failing to adjust for deductions can result in penalties. Double-check your math—or work with a tax professional.
Income from gig work, cryptocurrency, rental properties, or even side hustles needs to be included in your calculations.
Some states also require quarterly estimated tax payments. Make sure you check your state’s tax website for rules and due dates.
Tax brackets, deduction limits, and credits change regularly. Using last year’s numbers without updating for the current year may lead to inaccurate payments.
💡 Tips for Staying on Track
Set aside a portion of each payment you receive into a “tax savings” account. Aim for 25–30% depending on your income level and state tax obligations.
Keep a spreadsheet or use accounting software like QuickBooks, Wave, or FreshBooks. This makes your quarterly calculations easier and more accurate.
A CPA or enrolled agent can help you estimate taxes accurately and ensure you're compliant year-round. They can also recommend deductions and strategies to lower what you owe.
Set recurring reminders in your phone, Google Calendar, or project management app. Don’t leave it to memory!
If you miss the deadline, the IRS may charge a penalty for underpayment as well as daily interest on the unpaid amount. The penalty is calculated based on how much you owe and how late your payment is.
That said, if you had a reasonable cause (such as a natural disaster, illness, or death in the family), you may be able to request penalty abatement. But it’s always better to pay on time.
Quarterly estimated taxes might seem like a hassle, but they’re an essential part of managing your finances when you're not subject to traditional payroll withholding. With the June 15 deadline quickly approaching, now is the time to get your numbers in order and avoid costly mistakes.
Whether you're a freelancer juggling multiple clients or a small business owner navigating variable income, taking the time to plan your estimated taxes can save you time, money, and stress in the long run.
If you're unsure about how much to pay or how to calculate your income accurately, don’t hesitate to reach out to a tax professional. A little guidance now can help you avoid big problems later.
The IRS may charge penalties and interest on the unpaid amount. It's best to make the payment as soon as possible and consider contacting the IRS if you had a valid reason for missing it.
Yes, you can. Overpayments will be applied toward your annual tax return. If you overpay significantly, you’ll receive a refund or apply the credit toward next year’s estimated taxes.
Usually, no. But if you also have side income (freelance, gig work, investments) and your withholdings don’t cover your total tax liability, you might need to make estimated payments.
Not necessarily. If your income varies throughout the year, you can use the Annualized Income Installment Method to match your payments to actual earnings per quarter.
The most common mistake is treating it informally—no job description, no timesheets, no W-2s, or paying in cash. This raises red flags with the IRS and can result in disallowed deductions or penalties. Always document everything and run payroll like you would for any employee.
Being audited is comparable to being struck by lightning. You don't want to practice pole vaulting in a thunderstorm just because it's unlikely. Making sure your books are accurate and your taxes are filed on time is one of the best ways to keep your head down during tax season. Check out Vincere's take on tax season!
This post is just for informational purposes and is not meant to be legal, business, or tax advice. Regarding the matters discussed in this post, each individual should consult his or her own attorney, business advisor, or tax advisor. Vincere accepts no responsibility for actions taken in reliance on the information contained in this document.
For business tax planning articles, our tax resources provides valuable insights into how you can reduce your tax liability now, and in the future.
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