Statement Sorter | General categorizing guide | Gig driver guide | Etsy/online seller guide
If you're self-employed, the IRS expects tax payments as you earn, not just once in April. Miss a quarter by too much and you can owe an underpayment penalty even if you pay everything by the filing deadline. The number every quarter comes down to the same thing: your net income so far, income minus deductible business expenses, which means the quarter's actual work is sorting a stack of bank and card transactions into categories, not doing tax math.
| Period covered | Payment due |
|---|---|
| Jan 1 - Mar 31 | April 15, 2026 |
| Apr 1 - May 31 | June 15, 2026 |
| Jun 1 - Aug 31 | September 15, 2026 |
| Sep 1 - Dec 31 | January 15, 2027 |
Dates shift slightly when the 15th lands on a weekend or holiday; always confirm the exact date on the current-year IRS Form 1040-ES instructions before you pay.
Estimated tax is based on your expected net self-employment income for the year: total income minus deductible business expenses, run through self-employment tax plus your regular income tax rate. Two common approaches:
| Approach | How it works |
|---|---|
| Safe harbor | Pay roughly 25% of last year's total tax liability each quarter (110% of last year's tax if your income was higher, per current IRS rules) - avoids a penalty even if this year's income moves around |
| Actual year-to-date | Total up this year's income and expenses through the quarter's end, apply your tax rate, subtract what you've already paid - more accurate if income changed a lot, but only as good as your category totals |
Either way, the actual-year-to-date approach (and sanity-checking the safe-harbor one) needs an accurate income-minus-expenses figure, and that's the part that eats an afternoon when three months of transactions are sitting unsorted in an export.
Statement Sorter takes the CSV export from your bank, PayPal, or card account and sorts every transaction into expense categories automatically, with an AI pass for anything the rules miss, so you get category totals you can hand straight to a 1040-ES worksheet or your preparer.
Drop in this quarter's statement, get categorized totals in under a minute. No bank login, no signup, free while in beta.
Try it on your statementThis is a general guide, not tax advice for your specific situation - safe-harbor percentages, deadline dates, and what counts as deductible can all vary by year and by state. Confirm current numbers on IRS Form 1040-ES or with a tax preparer before you pay.