Your Takeaways:

  • There are certain dates to be aware of to pay estimated taxes throughout the year
  • Calculating your estimated taxes can be relatively straightforward with the right tools
  • When you file for a tax extension, you also need to pay any taxes you owe at that time

When it comes to tax extensions, there's a critical step that often gets overlooked: calculating your estimated taxes. It's not just about getting extra time to file – it's also about accurately figuring out how much tax you owe to avoid penalties later on. This is especially relevant for people with varied income streams, like freelancers, or anyone experiencing significant financial changes from the previous year.

In this guide, we’re going to break down the process of calculating estimated taxes for a tax extension. We’ll start by clarifying what a tax extension really means, and then move onto how to estimate your taxes. You'll get a step-by-step method to work out your tax liability, along with some pointers on submitting your payment.

This post aims to give you the essential information, no fuss, no muss, so you can handle your tax extension confidently and with minimal stress.

Understanding Tax Extensions

What is a Tax Extension?

A tax extension is essentially a request for more time to file your federal income tax return. The key point here is that it’s about filing, not paying. You’re asking the IRS for an additional six months to submit your paperwork, which moves the deadline from April 15th to October 15th. Remember, this doesn't grant extra time to pay any taxes you owe.

Who Can Apply for a Tax Extension?

Anyone can apply for a tax extension, and the process is surprisingly simple. You don’t need to explain why you need more time; the IRS grants this automatically if you file the proper form (Form 4868). It's a useful option if you're still gathering financial documents or dealing with unexpected life events.

Estimated Tax Deadlines

The quarterly deadlines for making estimated tax payments are as follows:

1st Payment: April 15th

2nd Payment: June 15th

3rd Payment: September 15th

4th Payment: January 15th of the following year

If any of these dates fall on a weekend or holiday, the deadline gets pushed out to the next business day.

Tax extensions are a helpful tool for buying extra time to file your return, but they don't alleviate your responsibility to pay what you owe by the original deadline.

In the next section, we’ll explore what estimated taxes are and why they're important in the context of a tax extension.

Understanding Estimated Taxes

Definition: Estimated taxes are periodic payments made towards your expected tax liability. They are especially important for individuals who don't have taxes withheld from their income, such as freelancers, self-employed individuals, or those with significant investment income.

Purpose: The IRS operates on a 'pay-as-you-go' system. If you don’t have taxes withheld from your income, or if withholding doesn't cover your full tax liability, you’re expected to make these payments. It ensures that you cover your tax liability throughout the year, rather than paying a lump sum at year-end.

Yellow paper with tax penalty written on it

Why Are Estimated Taxes Important?

Avoiding Penalties: Failing to make estimated tax payments, or underpaying these taxes, can lead to penalties. The IRS requires you to pay at least 90% of your current year’s tax liability or 100% of the tax shown on your previous year’s return (110% if your adjusted gross income is over a certain threshold).

Cash Flow Management: For individuals with irregular income, like freelancers or small business owners, estimated tax payments help manage cash flow by spreading tax payments throughout the year.

Tax Extension Implications: When you file for a tax extension, you're only extending the deadline to file your tax return, not the deadline to pay your taxes. Thus, accurately calculating and paying estimated taxes by the original deadline (April 15th) with your tax extension is vital to avoid interest and penalties.

Now, let’s walk through how to calculate your estimated taxes, step-by-step.

How to Calculate Your Estimated Taxes

Calculating your estimated taxes might seem intimidating, but it’s pretty manageable once you break it down. Here’s how you can do it.

A. Determining Your Expected Annual Income

Start by estimating your income for the year. This includes all earnings from self-employment, freelancing, investments, rental properties, and any other sources without tax withholdings.

Example: Let’s say you're a freelance graphic designer. You estimate earning $50,000 this year from various projects.

B. Calculating Taxable Income

From your estimated income, subtract any deductions you plan to claim. This could be business expenses for freelancers, health insurance costs, contributions to retirement accounts, etc.

Continuing our example: If you have $10,000 in deductible business expenses, your taxable income would be $50,000 - $10,000 = $40,000.

C. Applying the Current Tax Rates

Now, apply the tax rates to your taxable income. You can find the latest tax brackets on the IRS website or use an online tax calculator for this.

For instance, if your taxable income of $40,000 falls in the 12% tax bracket, your estimated tax could be around $4,800. But remember, tax rates are progressive, so only the income above each bracket's threshold is taxed at the higher rate.

D. Accounting for Self-Employment Tax

If you’re self-employed, remember to include self-employment tax, which covers Social Security and Medicare. As of the last update, this rate is about 15.3% of your net earnings.

For our example: 15.3% of $40,000 is $6,120.

E. Adding It All Up

Add your income tax estimate to your self-employment tax to get your total estimated tax.

In our example: $4,800 (income tax) + $6,120 (self-employment tax) = $10,920.

F. Dividing Into Quarterly Payments

Finally, divide your total estimated tax by four to get your quarterly payment amount.

For our example: $10,920 ÷ 4 = $2,730 per quarter.

Help From

Now that you know how to calculate your estimated taxes, you're much better prepared to file a tax extension to get an additional 6 months to file your taxes. Get started here.

Image of pen and calculator over Form 1040

Submitting Your Estimated Tax Payment

Submitting your estimated tax payments is a straightforward process, and you have several options:

Online Payments Through IRS Direct Pay: You can pay directly from your bank account for free using the IRS Direct Pay system. This method is secure and allows you to receive immediate confirmation of your payment.

Electronic Federal Tax Payment System (EFTPS): EFTPS is another electronic payment option, which is especially useful for business owners. You'll need to enroll in this system in advance, and once registered, you can schedule payments up to 365 days in advance.

Mobile App: The IRS2Go app allows you to make payments directly from your mobile device.

Credit or Debit Card Payments: You can also pay via credit or with debit card through third-party payment processors. Note that there may be a convenience fee associated with these services. 

Mailing a Check or Money Order: 1040-ES payment voucher. Make sure to include your Social Security number, phone number, and the tax period on the check.


There you have it! While handling estimated taxes and extensions can be straightforward with the right approach, remember that tools like can further simplify the process. By staying informed and organized, you can manage your tax responsibilities with confidence.

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