If you expect to owe at least $1,000 in federal taxes and don't have an employer withholding taxes, you need to make estimated tax payments four times a year. The due dates are typically April 15, June 15, September 15, and January 15. Use Form 1040-ES to calculate and submit payments. Skipping estimated payments can result in an underpayment penalty even if you pay everything when you file. Self-employed individuals, landlords, and investors are the most common people who need to pay estimates.