If you get a paycheck with taxes already withheld, you can skip this one.
But if you're freelancing, driving for a rideshare, or running a side hustle out of your garage, the IRS is expecting money from you four times a year — and the next deadline is closer than you think.
The system is pay-as-you-go, which means Uncle Sam wants his cut as the money comes in, not just in April.
Miss a quarterly payment and you could owe a penalty, even if you're owed a refund when you file your annual return.
That trips up a lot of first-time 1099 workers.
Generally, if you expect to owe at least $1,000 in federal tax for the year and your withholding covers less than 90% of what you owe, the IRS wants quarterly payments.
That includes gig workers, independent contractors, small business owners, landlords, and anyone earning serious income from investments or dividends.
You take your expected adjusted gross income, estimate your tax, subtract credits and any withholding, and divide what's left across four payments.
If that sounds like a headache, the IRS Direct Pay tool and free online calculators can walk you through it.
Many tax software programs will estimate the numbers for you too.
The deadlines land on a schedule that catches people off guard: roughly mid-April, mid-June, mid-September, and mid-January of the following year.
Notice that gap between January and April — that's not four equal quarters.
The IRS uses its own calendar, and it doesn't line up with the actual seasons.
If you underpay, the penalty is essentially interest on the money you should have sent in, calculated from the date it was due.
With current rates still elevated compared to the rock-bottom years of the last decade, that penalty isn't free money anymore.
You're basically paying the government interest for the privilege of holding onto cash you owed them.
The flip side is worth saying out loud: overpay all year and you've handed the IRS an interest-free loan.
They'll return it as a refund, but that money could have been sitting in a high-yield savings account earning 4% or more, or paying down a credit card charging 20%+.
A few practical moves can keep you out of trouble.
Set aside a percentage of every payment you receive — many freelancers use 25% to 30% as a rough starting point — into a separate savings account.
Then the quarterly bill doesn't feel like a surprise.
You can also increase withholding on a W-2 job to cover side income, which some people find easier than remembering four dates.
If you realize you've missed a payment, don't panic and don't ignore it.
You can send in a catch-up payment, and the IRS offers a safe harbor: if you pay at least 100% of last year's tax liability (110% if your income was high), you generally avoid the underpayment penalty, even if you owe more this year.
One more thing worth checking: if your income jumped this year, your prior-year safe harbor may not cover you, so run the numbers rather than assuming.
And if you live in a state with income tax, most states run their own estimated payment system with different deadlines.
Don't assume federal compliance means you're square with your state.
The bottom line is that quarterly taxes are less about the IRS being greedy and more about avoiding a nasty bill in April.
Final Thoughts
Pay a little at a time, keep it in a separate account, and you'll sleep better than the person who spent it all and got a letter.