Year-End Filing Deadlines for Small Employers (2026 Forms)

Year-end for a small employer is about six weeks of deadlines, most of them on the last day of January and the last day of February, with a few stragglers into March. The dates below are for 2026 income, meaning forms issued in early 2027, and the weekend rule has already been applied: January 31 and February 28, 2027 both fall on Sundays, which pushes the two biggest dates to a Monday. If you employ in both countries, the two calendars interleave, and the sequence is the same either way: close the books, issue the copies, file the government copy, keep the record.

December: before the last payroll

Two things decide which year a payment belongs to, and both catch people. In the US, wages are reported in the year of the pay date, not the pay period, so a check dated January 2, 2027 for December 2026 work is 2027 income and 2027 W-2 wages. Canada follows the same rule for T4 box 14. Decide your final 2026 pay date now, and treat anything after it as next year.

Then reconcile before the forms exist. Every employee's December pay stub should show YTD gross, YTD tax, YTD CPP or Social Security, and YTD EI or Medicare that match your payroll register and your remittances for the year; a difference found in December is an adjustment on the last payroll, while the same difference found in February is a corrected slip. Subscribers on Paystub Pilot get a per-employee year-end summary in the dashboard that totals every stub generated during the year, which is the figure set the forms are built from. Confirm you hold a W-9 for every US contractor you paid $2,000 or more by cash, check or transfer during 2026 (the threshold was $600 for 2025 payments), and a SIN or business number for every Canadian contractor paid more than $500. Missing TINs in December are a phone call; missing TINs in January are backup withholding and penalties.

January 15, 2027

US: fourth-quarter estimated tax for self-employed owners. Canada: the December remittance for regular remitters, and the October-to-December remittance for quarterly remitters. The 2027 CPP, EI and federal and provincial tax figures took effect on January 1, so the first January payroll runs on new tables; the CRA publishes the T4127 update in November and the SSA the new wage base in October.

February 1, 2027 (the January 31 deadline)

In the US, Form W-2 Copies B, C and 2 are due to employees and Copy A with Form W-3 to the SSA, with no extension available except for hardship on Form 8809. Form 1099-NEC Copy B is due to each contractor and Copy A to the IRS. Form 1099-MISC Copy B is due to recipients (other than the box 8 and 10 cases). Form 941 for the fourth quarter of 2026 is due, and so is Form 940, the annual FUTA return, and Form 945 if you did any backup withholding on 1099 payments. Most states with income tax want their copy of the W-2 and 1099-NEC by the same date; a few are later.

The employee and recipient copies do not have to be the government form. Under Publication 1141 and the 1099 general instructions they can be black-ink substitutes on plain paper with the same boxes and the same back-of-form instructions, which is what the W-2 and 1099-NEC generators produce for one recipient at a time: enter the year's figures, check the computed boxes in the free preview, and download the copies for $4.99 each or with a subscription. Copy A is separate. It is scanned, so it must be the red-ink original or an approved substitute, and if you file 10 or more information returns of any type in the year it must be electronic anyway. The SSA's Business Services Online takes W-2s and creates the W-3; the IRS's IRIS portal takes 1099s. Both are free and both are less work than paper even under the threshold.

February 16, 2027 (the February 15 deadline)

Form 1099-MISC to recipients when the form reports only box 8 (substitute payments in lieu of dividends or interest) or box 10 (gross proceeds paid to an attorney). February 15 is Presidents' Day, a legal holiday, so the deadline moves to the next business day. Everything else was due February 1.

March 1, 2027 (the last day of February)

Canada's day. T4 slips are due to employees, and the T4 slips with the T4 Summary to the CRA. T4A slips are due to recipients and, with the T4A Summary, to the CRA. Owner-managers who paid themselves dividends in 2026 owe a T5 slip and summary by the same date. Quebec employers issue the RL-1 to each Quebec employee and file the slips and RL-1 Summary with Revenu Québec, again on the same date; the T4 page shows the Quebec figures beside the slip. The CRA requires electronic filing once you file more than five slips of one type, counted separately for T4s, T4As and T5s; its Web Forms service handles up to 100 slips for free. Revenu Québec sets its own rule for RL slips, also more than five of one type.

As with the US forms, the recipient copies can be substitutes carrying the same boxes and instructions, and the T4 and T4A generators produce the two recipient copies for one employee or payee with the year's CPP, CPP2 and EI ceilings applied. The Summary and the CRA copy are still yours. The T4 box guide and the T4 vs T4A guide cover what goes in them.

In the US, March 1 is also the paper-filing deadline for Form 1099-MISC Copy A with Form 1096, for anyone under the 10-return e-file threshold who insists on paper.

March 31, 2027

Form 1099-MISC Copy A due to the IRS when filed electronically. This is the last of the year-end information-return dates; from here the calendar moves on to first-quarter 941s (April 30) and the April 15 remittance.

After the deadline: corrections and records

A wrong W-2 already filed with the SSA is fixed with Form W-2c and W-3c; a wrong 1099 with a corrected return through IRIS or on paper marked CORRECTED. A wrong T4 or T4A is amended by filing an amended slip electronically that repeats every box from the original with the wrong ones corrected, or cancelled and reissued. The penalty clocks reward speed: US information-return penalties for 2027 filings are $60 per form if corrected within 30 days, $130 by August 1, and $340 after, charged separately for the government copy and the recipient copy, with intentional disregard at $690 or 10% of the amount. The CRA's late-filing penalty for information returns starts at $100 and scales by the day and by slip count to $7,500, with a separate penalty from $125 for filing six or more slips of one type on paper.

Keep the employer copy of every form, the summaries, and the payroll records behind them for four years in the US (IRS employment-tax rule) and six years in Canada (CRA), counted from the end of the year the return relates to. The December pay stubs are part of that file; the stub-to-W-2 guide is what an employee will use to check your work in February, and it is a fair test to run yourself before the forms go out.