2027 Tax Deadline Calendar for Sole Proprietors
All IRS due dates that apply to sole proprietors in 2027, including Schedule C filing, quarterly estimated tax payments, and 1099 reporting deadlines.
Sole proprietors report business income on Schedule C, filed with Form 1040. You must also pay self-employment tax (Social Security and Medicare) on net earnings over $400. Quarterly estimated payments are required if you expect to owe $1,000 or more.
Showing 11 deadlines for Sole Proprietor
Next Deadline
Q4 2026 Estimated Tax Payment Due
265 days
Jan 15
January 2027
Q4 2026 Estimated Tax Payment Due
PaymentFinal quarterly estimated tax payment for 2026
February 2027
W-2 and 1099-NEC Filing Deadline
InformationEmployers must send W-2s to employees and file with SSA. 1099-NECs due to contractors and IRS. Moved from January 31 (Sunday) to the next business day.
March 2027
1099 Forms Due (Paper Filing)
InformationPaper-filed 1099-MISC, 1099-INT, 1099-DIV due to IRS (electronic deadline is March 31). Moved from February 28 (Sunday) to the next business day.
1099 Forms Due (Electronic Filing)
InformationElectronically-filed 1099-MISC, 1099-INT, 1099-DIV due to IRS
April 2027
Individual Tax Return Due
FilingForm 1040 due for individuals, including Schedule C for sole proprietors and single-member LLCs
Q1 2027 Estimated Tax Payment Due
PaymentFirst quarterly estimated tax payment for 2027
Individual/C-Corp Extension Deadline
ExtensionFile Form 4868 (individuals) or Form 7004 (C-Corps) to request 6-month extension
IRA/HSA Contribution Deadline
PaymentLast day to make 2026 IRA or HSA contributions
June 2027
Q2 2027 Estimated Tax Payment Due
PaymentSecond quarterly estimated tax payment for 2027
September 2027
Q3 2027 Estimated Tax Payment Due
PaymentThird quarterly estimated tax payment for 2027
October 2027
Extended Individual & C-Corp Returns Due
FilingExtended Form 1040 and Form 1120 returns due
Key Tax Tips for Sole Proprietors
Quarterly Estimated Payments
As a sole proprietor, you must pay estimated taxes quarterly using Form 1040-ES. Missing payments triggers an underpayment penalty even if you file on time.
1099-NEC Reporting
If you paid any contractor $2,000 or more during the year, you must file 1099-NEC by February 1, 2027 (moved from January 31, which falls on Sunday). Late filing incurs penalties of $60-$310 per form.
Schedule C with Form 1040
Your business income flows through Schedule C to your personal Form 1040, due April 15. Keep receipts organized throughout the year to maximize deductions.
2027 Quarterly Estimated Tax Schedule
| Quarter | Income Period | Payment Due |
|---|---|---|
| Q4 2026 | Sep 1 - Dec 31, 2026 | January 15, 2027 |
| Q1 2027 | Jan 1 - Mar 31, 2027 | April 15, 2027 |
| Q2 2027 | Apr 1 - May 31, 2027 | June 15, 2027 |
| Q3 2027 | Jun 1 - Aug 31, 2027 | September 15, 2027 |
| Q4 2027 | Sep 1 - Dec 31, 2027 | January 15, 2028 |
Sole Proprietor Tax Deadline FAQs
When is the tax filing deadline for sole proprietors in 2027?
Sole proprietors file Schedule C with Form 1040, due April 15, 2027 for the 2026 tax year. You can request a 6-month extension using Form 4868, which moves the filing deadline to October 15, 2027. However, you must still pay any taxes owed by April 15.
Do sole proprietors have to make quarterly estimated tax payments?
Yes, if you expect to owe $1,000 or more in taxes for the year. Quarterly payment dates for 2027 are: January 15 (Q4 2026), April 15 (Q1), June 15 (Q2), and September 15 (Q3). Use Form 1040-ES to calculate and submit payments.
What happens if a sole proprietor misses a quarterly payment?
The IRS charges an underpayment penalty calculated as interest on the missed amount. The penalty applies separately to each missed quarter. You can avoid penalties by paying at least 90% of current year taxes or 100% of prior year taxes (110% if AGI exceeds $150,000).
Do sole proprietors need to file 1099 forms?
Yes. If you paid any independent contractor $2,000 or more during the year, you must file Form 1099-NEC by February 1, 2027 (moved from January 31 due to the weekend). Paper-filed 1099-MISC forms are due March 1, and electronically-filed 1099-MISC forms are due March 31.
Can sole proprietors deduct home office expenses?
Yes, sole proprietors can deduct home office expenses on Schedule C using either the simplified method ($5 per square foot, up to 300 sq ft) or the regular method (actual expenses proportional to office space). These deductions reduce both income tax and self-employment tax.
Official IRS References
- IRS Publication 509: Tax Calendars
Official IRS calendar of tax deadlines
- IRS Estimated Taxes Guide
Information on quarterly estimated tax payments
- IRS: When to File
Filing deadlines and extension information
Deadlines may change due to holidays, weekends, or IRS announcements. Always verify current deadlines on IRS.gov.