Last Updated: May 2026
TL;DR: The IRS does not send reminders. If you are self-employed in 2026 you owe estimated taxes four times per year. Missing a deadline costs you an 8 percent annualized penalty on the underpaid amount. The Q2 deadline is June 15, 2026.
According to IRS Publication 505, self-employed workers must pay estimated taxes on this schedule:
You must pay quarterly estimated taxes if you expect to owe at least $1,000 in taxes for the year after subtracting withholding and credits. This applies to freelancers, independent contractors, gig workers, sole proprietors, and LLC owners who do not have taxes withheld from a paycheck.
Workers with a regular W-2 job who also do significant freelance work may also need to make estimated payments if their employer withholding does not cover the full tax liability on the side income.
The safest approach is the safe harbor method: pay at least 100 percent of last year's tax bill divided by four each quarter. High earners with adjusted gross income above $150,000 must pay 110 percent of last year's bill to qualify for safe harbor. If your income this year is significantly higher you may owe more at tax time but you will not be penalized.
Self-employment tax alone is 15.3 percent on your net earnings, 12.4 percent for Social Security and 2.9 percent for Medicare. Add your income tax bracket on top of that. Most self-employed workers should set aside 25 to 30 percent of every dollar earned for taxes.
Use the Vanderflip quarterly tax calculator to estimate what you owe for the next quarter.
The IRS currently charges 8 percent annualized interest on underpaid estimated taxes. On a $5,000 underpayment that is approximately $100 per quarter in penalties, money that goes directly to the IRS instead of staying in your account. The penalty is calculated separately for each quarter, so missing one deadline costs you regardless of how much you pay later in the year.
The easiest method is IRS Direct Pay at IRS.gov, which is free and confirms payment immediately. You can also use the Electronic Federal Tax Payment System (EFTPS), pay by debit or credit card through approved processors (with fees), or mail a check with Form 1040-ES voucher. Whatever method you choose, save the confirmation - you will need it at year-end when filing your return.
This article is for informational purposes only and does not constitute professional financial, legal, or tax advice. Data is sourced from publicly available government reports and updated as conditions change. Consult a qualified licensed professional before making financial decisions.
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