Estimates
7 min read
Quarterly estimated taxes for freelancers, explained
Who has to pay them, how much, and the four dates that matter in 2026 and 2027.

Who has to pay
If you work for yourself and expect to owe at least $1,000 in federal tax when you file, the IRS expects you to pay during the year instead of all at once in April. Nobody withholds tax from a client payment, so the job falls to you.
Most freelancers cross that line in their first year with more than about $8,000 of profit, because self-employment tax alone is 15.3 percent of most of your net earnings.
The four dates
For the 2026 tax year the payments are due April 15, June 15 and September 15, 2026, and January 15, 2027. When a date falls on a weekend or a federal holiday, the deadline moves to the next business day.
The quarters are not equal lengths. The second covers only April and May, which is why June feels early.
How much to pay
Add up the federal income tax and self-employment tax you expect for the year, subtract anything withheld from a W-2 job, and divide what is left by four. Ashford does this every time a payment lands and shows the running figure on your Estimates page.
How to pay
You can pay through IRS Direct Pay or your IRS online account at no cost, or by debit card through a processor that charges a small fee. Keep the confirmation number. Ashford records it against the quarter so it is on your return in April.
Connect the accounts you get paid through and Ashford shows your fourth-quarter estimate in about five minutes. Bookkeeping and estimates are free; filing starts at $24 a month.