Who is generally required to make estimated quarterly tax payments?

The IRS requires estimated quarterly payments from anyone who expects to owe at least $1,000 in tax after accounting for withholding and credits. For the 2025 tax year, the four deadlines are April 15, June 16, September 15, and January 15, 2026. Failing to pay adequate estimated taxes can result in an underpayment penalty. Self-employed individuals, gig workers, freelancers, real estate investors, and retirees with pension income are among the most common groups required to make estimated payments. A safe harbor exists: paying 100% of the prior year's tax liability (or 110% for higher-income taxpayers) avoids penalties regardless of what you actually owe.