Unreported 1099 income almost never goes unnoticed. If you don’t report 1099 income, the IRS will very likely find out. Every 1099 your clients send also goes to the IRS, and its computers match those forms against your tax return. Usually, about a year or two later, you get a letter called a CP2000. It … Read more
Paying quarterly taxes with irregular income is easier than it looks. You don’t have to split your tax into four equal payments. Instead, you can pick one of three IRS-approved methods: pay a fixed amount based on last year, pay a share of whatever you earn each quarter, or use the annualized income method to … Read more
Use this underpayment penalty calculator to see what a late or missed estimated tax payment will cost you. The IRS penalty works like interest. For 2026, it runs at 6% to 7% a year on the amount you underpaid, for each day it was late. Missing a $3,000 payment in June and paying it with … Read more
The safe harbor rule is the IRS’s promise that you won’t pay an underpayment penalty, as long as you pay a minimum amount on time during the year. For freelancers with unpredictable income, it’s the single most useful rule for quarterly estimated taxes. The key word is penalty. The safe harbor protects you from the … Read more
The estimated tax due dates for the 2026 tax year are April 15, June 15 and September 15, 2026, and January 15, 2027. Miss one and the IRS starts charging interest on what you owe, even if you pay everything in April. Below you’ll find the dates for 2026 and 2027, the other tax deadlines … Read more
Quarterly estimated taxes are how freelancers pay the IRS during the year, since no employer withholds tax from their income. Instead of one big bill in April, you send four payments, each covering part of the year’s income tax and self-employment tax. Quick answer: If you expect to owe $1,000 or more when you file, … Read more