The Small-Business Employee Benefits Compliance Calendar

If you offer benefits to your team, you're on the hook for a handful of deadlines and filings throughout the year — and missing them can mean penalties, even if your coverage itself is solid. The tricky part is that which rules apply to you depends on your size and your plan type. This guide lays out the key dates in plain language and flags what applies to whom, so nothing sneaks up on you.

This is a general overview for educational purposes, not legal or tax advice. Exact deadlines depend on your plan year, plan type, and size, and some dates shift year to year. Confirm your specific obligations with your benefits advisor, CPA, or ERISA counsel.

First: does this even apply to me?

Two factors decide most of your obligations:

• Your size. The ACA "employer mandate" and its reporting (Forms 1094-C/1095-C) apply to Applicable Large Employers (ALEs) — generally those with 50 or more full-time-equivalent employees. If you're under 50 FTEs, most of the ACA reporting burden doesn't apply to you — but several other items below still do.
• Your plan type. Some rules only hit self-funded or level-funded plans (like the PCORI fee and certain filings), while others apply to any employer sponsoring a plan.

Keep those two lenses in mind as you read.

The calendar, by time of year

Year-round / at open enrollment (employers with an applicable group health plan)

• Summary of Benefits and Coverage (SBC): provide to employees at open enrollment and on request.
• Section 125 elections: if you run pre-tax payroll deductions through a cafeteria plan, elections are made before the plan year starts and are generally locked in absent a qualifying event. See our Section 125 overview [blocked].
• Required notices: Required notices may include CHIP, Women's Health and Cancer Rights, Newborns' and Mothers' Act, and Summary Plan Description disclosures, depending on the plan and applicable triggering conditions.

By October 15 each year — Medicare Part D notice (most employers with a drug plan)

If your health plan includes prescription drug coverage and you have any Medicare-eligible employees or dependents, you must send a Medicare Part D "creditable coverage" notice by October 15, before the Medicare Annual Enrollment Period begins. This one is widely missed by small employers because it's easy to forget and applies even to small groups.

January 31 — W-2 health coverage reporting (larger filers)

Employers filing 250 or more W-2s must report the aggregate cost of employer-sponsored health coverage in Box 12, Code DD, on employees' W-2s, due January 31. Smaller employers are currently exempt.

Late February / early March — ACA furnishing (ALEs, 50+ FTEs)

For the prior calendar year's coverage, ALEs must furnish Form 1095-C to full-time employees by March 2. For certain eligible recipients and circumstances, an IRS alternative furnishing method permits a website notice stating that the employee may request Form 1095-C and receive it within 30 days; follow the IRS eligibility, posting-date, and retention requirements. (For the 2025 tax year, that furnishing deadline was March 2, 2026.)

March 31 — ACA e-filing with the IRS (ALEs, 50+ FTEs)

ALEs generally must electronically file Forms 1094-C and 1095-C with the IRS when filing 10 or more information returns in aggregate. For the 2025 tax year, the electronic-filing deadline was March 31, 2026.

Within 60 days of your plan year start — Part D disclosure to CMS

Separately from the employee notice, employers must disclose their plan's creditable-coverage status to CMS online within 60 days after the start of each plan year (for a calendar-year plan, that's roughly the end of February / early March), and again within 30 days of any change.

July 31 — Form 5500 and the PCORI fee

• Form 5500 (ERISA): generally required for plans with more than 100 participants at the beginning of the plan year, and for certain funded plans or other plans not eligible for the small-plan exemption. For calendar-year plans it's due July 31, with a 2½-month extension to October 15 available via Form 5558. Many small, fully-insured plans are exempt — but don't assume; confirm.
• PCORI fee: if you sponsor an applicable self-insured plan (many level-funded arrangements are self-insured), the annual fee is reported on IRS Form 720 and generally due July 31 of the subsequent calendar year following the plan year.

Setting employee contributions — the affordability check (ALEs)

When you decide how much employees pay for coverage, ALEs need to keep the ACA affordability threshold in mind to avoid penalties. That percentage is adjusted annually — for the 2026 plan year it rose to 9.96% of income (up from 9.02% for 2025) for the lowest-cost, self-only plan. Check the current year's number when you price contributions.

Before plan year-end — nondiscrimination testing

If you offer a Section 125 cafeteria plan or FSA, nondiscrimination testing should be completed before the plan year ends to confirm the plan doesn't favor highly compensated employees.

Why this matters for a growing business

Two moments trip up Southwest Florida employers most often:

1. Crossing 50 full-time-equivalent employees. When an employer is determined to be an ALE for a calendar year, a set of ACA obligations applies for that year; ALE status generally uses the prior calendar year's average workforce — offering affordable, minimum-value coverage to full-time staff, plus the 1094-C/1095-C reporting above. If you're a growing contractor near that line, plan ahead; seasonal and variable-hour workers make the FTE math genuinely tricky. (Our ICHRA guide [blocked] covers one flexible way growing employers offer coverage.)
2. Switching to a self-funded or level-funded plan. Alternative funding is a great cost move — see our group health insurance [blocked] page — but it adds items like the PCORI fee and, often, Form 5500. Worth it, but know what comes with it.

How we help

We build a compliance calendar tailored to your size and plan type, so you know exactly what's due and when — and we handle the strategy so the deadlines serve a plan that's actually saving you money. If you'd like yours mapped out, contact us [blocked] or call (239) 273-9173.

Frequently Asked Questions

Which benefits compliance rules apply to a business with fewer than 50 employees? Most ACA employer-mandate reporting (1094-C/1095-C) does not apply under 50 FTEs. But you may still owe the Medicare Part D creditable-coverage notice, must provide SBCs and required plan notices, and may owe the PCORI fee and Form 5500 depending on your plan type and size.

When are ACA 1095-C forms due? For ALEs, forms are furnished to employees by March 2 (or made available on request under the alternative method) and e-filed with the IRS by March 31. For the 2025 tax year those dates were March 2, 2026 and March 31, 2026.

What is the Medicare Part D notice deadline? Employers with prescription drug coverage must send the creditable-coverage notice to Medicare-eligible individuals by October 15 each year, and disclose status to CMS within 60 days of the plan year start.

Do small businesses have to file Form 5500? Generally, Form 5500 reporting applies to plans with more than 100 participants at the beginning of the plan year, plus certain funded plans or plans not eligible for the small-plan exemption. Many small fully-insured plans are exempt — but confirm your situation, since exemptions depend on plan structure.

Roger Aboytes is the founder of Vantage Pointe Consulting, helping Southwest Florida businesses build benefits programs that are compliant and cost-effective. This article is educational and not legal or tax advice. Last reviewed: September 2026.