The HR Compliance Calendar Small Businesses Need for Late 2026 and 2027

What Deadlines Does a Small Business Actually Face in Late 2026 and 2027?

Here is the short answer. If you employ fewer than 50 people in the US, your must-hit deadlines are: W-2s and 1099-NECs by February 1, 2027, quarterly Form 941 filings, OSHA Form 300A posting from February 1 to April 30, 2027 (if you have more than 10 employees), your state's minimum wage changes on January 1, 2027, and your state's pay transparency and retirement plan mandates.

You can probably skip EEO-1 and ACA forms entirely. Most compliance calendars never tell you that, because they are written for 500-person companies. This one is written for you.

An HR compliance calendar is a month-by-month list of the filing, posting, and payment deadlines an employer must meet under federal and state law. It covers tax forms like W-2s and 1099s, workplace reports like OSHA's Form 300A, and state rules on pay transparency, minimum wage, and retirement plans.

Which Federal Deadlines Apply to Companies Under 50 Employees?

Before you copy someone else's checklist, run this triage. Half the scary acronyms do not apply to you.

• EEO-1 report: Only private employers with 100 or more employees, or federal contractors with 50 or more, must file. Under 50 with no federal contracts? You are exempt. Even better: the EEOC sent a proposed rule to rescind EEO-1 reporting entirely in May 2026, per Jackson Lewis. Larger employers should still watch the EEOC data collections page, since the 2025-data filing window had not opened as of mid-2026.
• ACA Forms 1094-C and 1095-C: Only Applicable Large Employers (50 or more full-time equivalents) must file, per the IRS. The exception: if you self-insure a health plan at any size, you file Forms 1094-B and 1095-B.
• W-2s, 1099-NECs, Forms 941 and 940: Everyone with employees files these. No size exemption.
• OSHA Form 300A: Employers with 10 or fewer employees all year are exempt from routine injury recordkeeping, and so are many low-hazard office industries, per OSHA. Everyone else posts the annual summary from February 1 to April 30.

Your Month-by-Month Compliance Calendar

September 2026

Florida's minimum wage hits $15.00 on September 30, 2026, the final step of its voter-approved schedule before annual inflation adjustments begin, per Paycom's state tracker. If you pay anyone in Florida, update payroll now, not on the 29th.

October and November 2026

Roughly 20 states adjust their minimum wage for inflation each January, and most announce the new rates in the fall. Watch your state labor department in October and November so your January 1 budget is real, not a guess. The DOL's state minimum wage page is the canonical list.

Q3 Form 941 is due November 2, 2026, because October 31 lands on a Saturday. Massachusetts employers: the annual HIRD form window opens November 15 and closes December 15.

December 2026

This is prep month, and it decides whether January is calm or chaotic.

1. Confirm every employee's legal name, SSN, and address for W-2s.
2. Collect W-9s from every contractor you paid $600 or more. December is also the right time to double-check worker status against the contractor vs employee classification rules, because misclassification surfaces fastest at 1099 season.
3. Order updated labor law posters for states with January changes.
4. California employers: if you still have not registered for CalSavers, do it now. The final deadline (employers with even one employee) passed on December 31, 2025, and fines start at $250 per eligible employee, per CalSavers.

January 2027

New minimum wages take effect January 1 in around 20 states. The headline change: Michigan reaches $15.00 per hour on January 1, 2027 under its Improved Workforce Opportunity Wage Act, per OnPay. Update pay rates, posters, and any job postings that list wages.

February 2027

The busiest month of the year for a small employer:

• February 1: W-2s to employees and the SSA, and 1099-NECs to contractors and the IRS. The usual January 31 deadline falls on a Sunday in 2027, so it rolls to Monday, per the IRS.
• February 1: Q4 Form 941 and annual Form 940 (FUTA), same Sunday rollover.
• February 1: Post OSHA Form 300A (your 2026 injury summary) where employees can see it. It stays up through April 30.

March 2027

If you are one of the few small employers with ACA duties (self-insured, or hovering at 50 FTEs): paper filing is due March 1, 2027 (February 28 is a Sunday), and only employers filing fewer than 10 total information returns may file on paper. Electronic filing is due March 31, 2027. You no longer have to mail 1095s automatically; posting a notice and providing forms on request satisfies the rule, per the IRS.

Also March 2: employers with 20 to 249 employees in designated higher-hazard industries (construction, manufacturing, healthcare, and others) must submit Form 300A data electronically through OSHA's ITA portal.

April 2027

Take down the 300A after April 30. Q1 Form 941 is due April 30. Then breathe.

Mid and Late 2027 Watch List

• July 31, 2027: Form 5500 if you sponsor your own 401(k) plan.
• September 26, 2027: Delaware's pay transparency law takes effect for employers with 25 or more employees.
• September 30, 2027: Florida's first CPI-based minimum wage adjustment after the $15 milestone.
• EEO-1: if the rescission has not been finalized, a filing window could still open for 100+ employers.

The Full Calendar in One Table

DeadlineDateWho must actUnder 50 employees? Florida minimum wage $15.00Sep 30, 2026Florida employersYes, if in FL Q3 Form 941Nov 2, 2026All employersYes MA HIRD formDec 15, 2026Massachusetts employersYes, if in MA State minimum wage changesJan 1, 2027Employers in ~20 statesYes W-2, 1099-NEC, Q4 941, Form 940Feb 1, 2027All employersYes OSHA 300A postingFeb 1 to Apr 30, 202711+ employees, covered industriesSometimes ACA paper filingMar 1, 2027ALEs and self-insured plansRarely OSHA 300A electronic submissionMar 2, 202720-249 in high-hazard industriesSometimes ACA electronic filingMar 31, 2027ALEs and self-insured plansRarely EEO-1 (if not rescinded)TBD by EEOC100+ employees or federal contractorsNo Delaware pay transparencySep 26, 202725+ employees in DESometimes

What State Rules Changed in 2026 That You Might Have Missed?

Two pay transparency laws took effect this summer: Virginia's on July 1, 2026 (pay info in postings plus a salary history ban), and Maine's on July 29, 2026 for employers with 10 or more employees, per Ogletree Deakins. They join California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington, and DC, which already require pay ranges in job postings. If you hire across state lines, work through the full US pay transparency checklist for employers before your next posting goes live.

On retirement: 16 states now run mandatory auto-IRA programs for employers without their own plan, per Betterment's 50-state guide. Minnesota's Secure Choice deadlines began phasing in during 2026, and Washington Saves is scheduled to launch in 2027. These mandates reach down to one-employee businesses in several states, so check yours even if you feel too small to matter.

How Do You Actually Stay Ahead of These Deadlines?

Three habits beat any printed calendar. First, put every date above into the shared calendar your team already checks, with a reminder two weeks out. Second, assign each deadline one named owner, even if that owner is you. Third, keep clean records year-round: most filings are painless when your time, pay, and attendance records meet wage and hour rules by default instead of through a December scramble.

Deadlines are not the hard part. Reconstructing a year of messy records in January is the hard part. If your time tracking, payroll, and leave data already live in one system, most of this calendar becomes a review task instead of a research project. That is exactly what the compliance and record-keeping features in TracefyHR are built to do for teams under 50 people.

Frequently Asked Questions

Do small businesses have to file an EEO-1 report?

No, unless you have 100 or more employees, or 50 or more and a federal contract. The EEOC has also proposed ending EEO-1 reporting altogether.

When are W-2s due in 2027?

February 1, 2027. The normal January 31 deadline falls on a Sunday, so it moves to the next business day. The same date covers 1099-NEC forms.

Do companies under 50 employees have to file ACA forms 1094 and 1095?

Usually not. ACA reporting applies to employers with 50 or more full-time equivalents, plus any employer that self-insures a health plan.

What is OSHA Form 300A and who has to post it?

It is the annual summary of workplace injuries. Employers with 11 or more employees in covered industries post it from February 1 to April 30 each year.

Which states require retirement plans for small businesses?

Sixteen states, including California (CalSavers), Illinois, Oregon, Colorado, and Minnesota, require employers without a plan to enroll workers in a state auto-IRA program.

What states require salary ranges in job postings in 2026?

California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington, DC, and now Virginia and Maine as of July 2026.

What happens if I miss a payroll tax deadline?

The IRS charges late filing and late deposit penalties that grow with time, starting around 2 to 5 percent and climbing to 15 percent for long delays.