Every deliverable ends the same way: with The Footnote. What follows is one, exactly as a client receives it.
If you expect to owe at least $1,000 in federal tax for the year, the IRS generally requires you to pay as you go through quarterly estimated payments.[1] For 2026, those deadlines fall in April, June, and September, with the final installment due the following January.[2] Miss or underpay one, and an underpayment penalty can apply — though safe-harbor rules protect you if you pay at least 90% of this year's tax or 100% of last year's (110% for higher incomes).[3] New York runs its own estimated tax system on a similar calendar, filed separately.[4] And if you're weighing an S-corp election to manage self-employment tax, the filing window is tight: generally two months and 15 days into the tax year you want it to take effect.[5]
Prepared by Anki AI. Reviewed and stood behind by Northline Office.
Claim audits use the same spine — every claim, judged against a source:
| Claim | Status | Source | Note |
|---|---|---|---|
| "Any freelancer has to pay estimated taxes." | Corrected | IRS — Estimated Taxes | Only if you expect to owe $1,000 or more in federal tax for the year. |
| "Estimated payments are due four times a year." | Verified | IRS — Form 1040-ES | April, June, and September, with the final due the following January. |
| "Once you underpay, a penalty is unavoidable." | Corrected | IRS — Publication 505 | Safe harbor: 90% of this year's tax, or 100% of last year's (110% above $150K AGI). |
| "You can elect S-corp status whenever it suits you." | Unsupported | IRS — Form 2553 instructions | The window is ~2 months and 15 days into the tax year the election takes effect. |
This is the standard every engagement ships to — the audits, the refreshes, the pilot.