Most tax-season stress is timing: the books are not closed, a form arrives late, a payment was forgotten. The steps below are ordered by when they need to happen, because the ones that save the most — planning decisions — have to be made before the year ends.
How we ordered them
- Calendar. Each step is placed where it has to happen, not where it is convenient.
- Primary-source dates. Federal dates from IRS Publication 509 and form instructions; Massachusetts from DOR.
The eight steps
1.Get the books current before year end
Best for: October to December
Planning needs real numbers. If the books are behind, catch them up in the fall so there is something to plan with.
Read more →2.Have a planning conversation before December 31
Best for: November to December
Equipment purchases, retirement contributions, the timing of income and expenses, and whether an entity change makes sense for next year all have to be decided while the year is still open.
Read more →3.Make the fourth-quarter estimated payment
Best for: Due January 15, 2027
The final 2026 federal estimated payment is due Friday, January 15, 2027. Massachusetts estimates follow the same quarterly schedule.
Read more →4.Issue W-2s and 1099-NECs
Best for: Due February 1, 2027
For 2026, W-2s and 1099-NECs are due Monday, February 1, 2027, because January 31 falls on a Sunday. The 1099-NEC threshold is $2,000 for payments made after December 31, 2025 — collect W-9s from contractors early so this is a report, not a scramble.
5.Gather the forms you receive
Best for: January to February
1099s, 1098s, K-1s, brokerage statements, health coverage forms. Make a list from last year's return of everything you expect, and tick them off.
Read more →6.Close the year and review the statements
Best for: January to February
Reconcile every account through December 31, review the profit and loss and balance sheet, and fix anything odd before it goes into a return.
Read more →7.File partnership and S corporation returns
Best for: Due March 15, 2027
Forms 1065 and 1120-S for calendar-year 2026 are due Monday, March 15, 2027. Owners need their K-1s to file personal returns, so this date drives everything after it.
8.File individual returns — or extend
Best for: Due April 15, 2027
Form 1040 and Massachusetts Form 1 for 2026 are both due Thursday, April 15, 2027. An extension extends the time to file, not the time to pay — estimate and pay what you owe by April 15.
Key dates for 2026 returns
| Date | What is due |
|---|---|
| January 15, 2027 | Fourth-quarter 2026 estimated tax |
| February 1, 2027 | W-2s to employees and SSA; 1099-NEC to recipients and IRS |
| March 15, 2027 | Partnership (1065) and S corporation (1120-S) returns |
| April 15, 2027 | Form 1040 and Massachusetts Form 1; first 2027 estimate |
Calendar-year taxpayers. Employers also file quarterly Massachusetts Paid Family and Medical Leave returns through MassTaxConnect.
General information, not advice for your specific situation. Tax rules, prices and product features change, and firms change what they offer — check with the provider before relying on anything here, and talk to us or another qualified professional before acting on it.
