Just the Tip:
If you’ll owe the IRS $1,000 or more after withholding this year, your third estimated payment is due September 15. Don’t guess the amount. Pay a quarter of last year’s total tax each installment, 110% of that if last year’s adjusted gross income topped $150,000, and the underpayment penalty can’t touch you whatever this year earns.
People don’t miss September 15 because they’re hiding from the IRS. They miss it because they’re trying to predict this year’s tax bill, which nobody can do in September, and the IRS doesn’t ask you to.
The safe harbor is an annual rule, and it’s the whole answer. You avoid the underpayment penalty when withholding plus estimated payments cover the smaller of 90% of this year’s tax or 100% of last year’s. The first is a guess. The second is printed on the total tax line of last year’s Form 1040. Divide it by four for each installment, September 15’s included.
Two qualifiers. If last year’s adjusted gross income topped $150,000 ($75,000 if married filing separately), the target is 110% of last year’s tax, a quarter of that per installment. And last year’s return must cover a full 12 months. Meet it and it doesn’t matter if your income doubled. The rest is due in April, penalty-free.
Who owes is a test, not a job title. Expect to owe $1,000 or more when you file, after withholding and refundable credits, and you’re supposed to pay quarterly. That covers freelancers and gig workers, but also landlords, retirees pulling from an IRA without withholding, and anyone who sold stock at a gain.
Paying takes five minutes at IRS Direct Pay, which is free, needs no login, and pulls from your bank account. Pick estimated tax (Form 1040-ES) and the current tax year. EFTPS works too if you already have an account.
If you skipped April or June, pay those now too. The penalty runs like interest, per installment, for every day it stays unpaid, so paying now stops a meter that January would leave running. If you also have a W-2 job, raise your withholding for the rest of the year. The IRS treats withholding as paid evenly across all four due dates, which backfills the ones you missed.
Then put the same amount on the calendar for January 15, with the full deadline calendar beside it. This year’s real bill becomes an April conversation instead of a September panic.
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