Why this matters.
When you work for yourself, no employer withholds tax from your pay, so the IRS expects you to pay as you go. If your net earnings from self-employment are $400 or more you must file a return (IRC §6017) and pay self-employment tax of 15.3% on 92.35% of your net earnings: 12.4% Social Security up to the annual wage base and 2.9% Medicare with no cap (IRC §1401 and §1402). On top of that you owe regular income tax. Most freelancers, gig workers and 1099 contractors who expect to owe $1,000 or more for the year must make quarterly estimated payments using Form 1040-ES, due April 15, June 15, September 15 and January 15.
Paying too little or too late triggers the underpayment penalty under IRC §6654, which works like interest and runs separately for each quarter. You can avoid it by meeting a safe harbor: paying at least 90% of this year’s tax, or 100% of last year’s (110% if last year’s adjusted gross income was over $150,000). Most states with an income tax have their own estimated payment rules too. This check shows whether your payments are on track and which deductions, such as half of your self-employment tax (§164(f)), the qualified business income deduction (§199A) and self-employed health insurance (§162(l)), you may be missing.