Quick answer
The four dates every freelancer needs are the quarterly estimated tax deadlines: for 2026 income, January 15, 2027 is the last one; for 2027 income they’re April 15, June 15 and September 15, 2027, and January 18, 2028. Your 2026 tax return is due April 15, 2027. If you pay contractors, send their 1099-NEC by February 1, 2027.
Complete calendar: October 2026 to January 2028
| Date | Deadline | Who it affects |
|---|---|---|
| October 15, 2026 | Extended 2025 individual returns due; last day for 2025 SEP IRA contributions if you filed an extension | Anyone who extended their 2025 return |
| November-December 2026 | ACA Marketplace open enrollment for 2027 health coverage | Self-employed buying their own insurance |
| December 31, 2026 | Last day to set up a Solo 401(k) for 2026 employee contributions; last day for 2026 business purchases to count as 2026 expenses | Freelancers planning year-end tax moves |
| January 15, 2027 | 4th estimated tax payment for 2026 (income Sept-Dec 2026) | All self-employed who pay estimated taxes |
| February 1, 2027 | Send Form 1099-NEC to contractors paid more than $2,000 in 2026 and file it with the IRS (January 31 falls on a Sunday) | Freelancers who hired contractors |
| February 1, 2027 | File your 2026 return and pay in full by this date to skip the January 15 payment without penalty | Optional alternative |
| March 15, 2027 | Partnership (Form 1065) and S-corp (Form 1120-S) returns for 2026 | Multi-member LLCs and S-corps |
| April 15, 2027 | 2026 individual tax return (Form 1040 with Schedule C and SE) and balance due; extension request (Form 4868); 1st estimated payment for 2027; last day for 2026 IRA and HSA contributions; 2026 SEP IRA contributions if not extending | Everyone |
| June 15, 2027 | 2nd estimated payment for 2027 (income April-May) | Self-employed |
| September 15, 2027 | 3rd estimated payment for 2027 (income June-August); extended partnership and S-corp returns | Self-employed, LLCs, S-corps |
| October 15, 2027 | Extended 2026 individual returns; last day for 2026 SEP IRA contributions with an extension | Anyone who extended |
| December 31, 2027 | Solo 401(k) setup and year-end planning for 2027 | Self-employed |
| January 18, 2028 | 4th estimated payment for 2027 (January 15 is a Saturday and January 17 is Martin Luther King Jr. Day) | Self-employed |
The deadlines explained
Quarterly estimated taxes
If you’ll owe $1,000 or more, you pay four times a year. The «quarters» cover uneven periods: January-March, April-May, June-August and September-December. Pay with IRS Direct Pay or your IRS Online Account. See Quarterly Estimated Taxes and How to Pay Online.
Tax day (April 15)
Your annual return (Form 1040 with Schedule C and Schedule SE) and any remaining balance are due. It’s also the deadline for the first estimated payment of the new year, so April is usually the most expensive month for freelancers: plan for both.
1099 deadlines
- If you pay contractors: send Form 1099-NEC to each contractor you paid more than $2,000 during 2026 (the new threshold; it was $600) and file it with the IRS by February 1, 2027.
- If you receive 1099s: clients and platforms send them around the same time. Compare them with your own records, and report all income whether or not you receive a form.
Extensions
Form 4868 gives you until October 15 to file, but not to pay. Estimate what you owe and pay it by April 15 to avoid the failure-to-pay penalty and interest.
Retirement contribution deadlines
| Account | Deadline to contribute for 2026 |
|---|---|
| Traditional or Roth IRA | April 15, 2027 |
| HSA | April 15, 2027 |
| SEP IRA | Your filing deadline, including extensions (up to October 15, 2027) |
| Solo 401(k) | Plan set up by December 31, 2026 for employee deferrals; contributions generally by the filing deadline, including extensions |
Weekend and holiday rule
When a deadline falls on a Saturday, Sunday or federal holiday, it moves to the next business day. That’s why the 1099 deadline is February 1, 2027, and the last 2027 estimated payment is January 18, 2028.
State deadlines
Most states follow the federal dates for returns and estimated taxes, but some differ. Check your state’s revenue department.
Never miss a deadline
- Add every date above to your calendar with a reminder one week before.
- Schedule estimated payments in advance with IRS Direct Pay.
- Keep 25-30% of each payment in a tax savings account so the money is ready.
- Sign up for our newsletter: we send a reminder before every quarterly deadline.
Frequently asked questions
When are quarterly taxes due in 2027?
April 15, June 15 and September 15, 2027, and January 18, 2028 for 2027 income.
When is the last estimated payment for 2026?
January 15, 2027. You can skip it without penalty if you file your 2026 return and pay the full balance by February 1, 2027.
Does an extension give me more time to pay?
No. It only gives you more time to file. Payment is still due April 15.
When do I send 1099s to my contractors?
By February 1, 2027 for payments made in 2026, to contractors paid more than $2,000.
This article is general information, not tax advice. Dates can change due to IRS announcements or disaster relief; check IRS.gov.
Sources
- One Big Beautiful Bill Act changes 1099 thresholds (Avalara): $2,000 1099-NEC threshold from 2026.
Deadlines follow IRS rules for estimated taxes (Form 1040-ES), information returns, individual and business returns and retirement contributions; weekday adjustments were calculated for 2026-2028.