At RR Capital, we've learned that tax season isn't a crisis if you mark your calendar early. We work with freelancers, agencies, tech founders and solo operators across Pennsylvania and beyond — and every one of them benefits from knowing these dates before January 1st.
Federal deadlines that matter in 2026
| Deadline | What's due | Who it affects |
|---|---|---|
| January 31 | W-2s to employees, 1099-NEC to contractors ($600+) | Employers & payers |
| March 16 | S-corp (1120-S) & partnership (1065) returns | Pass-throughs |
| April 15 | Individual 1040s, C-corp 1120s, Q1 estimated taxes | Sole props, S-corps, C-corps |
| June 15 | Q2 estimated tax payments | Self-employed & investors |
| September 15 | Q3 estimates, extended pass-through returns | Self-employed, partnerships |
| October 15 | Extended individual returns (6-month extension) | Anyone who filed for extension |
Pennsylvania specifics
If you're operating in PA, add these to your calendar:
- PA-40 ES (quarterly) follows federal quarterly due dates — same April 15, June 15, Sept 15, Jan 15
- PA requires filing by May 31 if you haven't gone federal yet (they move faster than IRS on enforcement)
- PA-41 for business entities is due 60 days after federal deadline for C-corps
- PA quarterly wage reports to Department of Labor & Industry (DOLI) — quarterly
Why January 31 catches everyone off guard
The contractor-form deadline arrives just four weeks after the holidays. If you paid any individual or unincorporated business $600 or more during the year, you owe them a 1099-NEC — and the IRS a copy. Late penalties start at $60 per form and climb fast.
What we tell clients: Collect a W-9 from every contractor before their first invoice. It turns January from a scramble into a mail merge. (Our Monthly Bookkeeping Spreadsheet has a tracker for exactly this.)
Extensions buy filing time — not payment time
An extension moves your filing deadline to October 15, but tax owed is still due April 15. If you expect to owe, estimate the amount and pay it when you file for extension. The IRS is flexible on deadlines — but not on payment.
Safe harbor rule: Pay 100% of last year's total tax (110% if AGI > $150k) in equal quarterly installments, and you're protected from underpayment penalties.
What RR Capital recommends right now
- Update your books — January 31 for prior year is fast approaching. Monthly reconciliation now makes year-end a breeze.
- Collect W-9s — from every contractor you've paid (or will pay). Do it now while Q4 is fresh.
- Verify your entity type — C-corp, S-corp, or sole prop? Deadline differences are real. See our tax strategy consultation if you're unsure.
- Flag quarterly obligations — if your business had solid profit, Q1 estimated tax is April 15.
- Review PA rules — many multi-state operators forget PA has tighter enforcement than federal.
Getting tight on time? RR Capital helps businesses go from "Oh no" to "organized" in 2–3 weeks. Schedule a tax review with our team — we work with agencies, tech teams, and solo founders.