Employer Benefits Compliance Checklist: The Deadlines and Filings to Track in 2026

• The Medicare Part D creditable coverage notice goes to Medicare-eligible people before the October 15 start of the Part D enrollment period (SHRM, 2026).
• Self-insured plans owe the PCORI fee of $3.84 per covered life for plan years ending October 1, 2025 through September 30, 2026, due July 31 (Paylocity, 2026).
• Form 5500 is due the last day of the seventh month after the plan year ends, and small unfunded or fully insured plans under 100 participants are exempt (The Horton Group).
• A cafeteria plan must exist as a written plan, and it must pass nondiscrimination tests or highly compensated and key employees lose the tax exclusion (26 U.S.C. 125).
• The 2026 ACA employer penalties are $3,340 and $5,010 per employee (IRS Revenue Procedure 2025-26).

Most employers do not miss a benefits deadline because they ignore it. They miss it because nobody owns the list. This checklist puts every recurring item in one place, says who it applies to, and shows the date so you can put it on a calendar today.

What does an employer benefits compliance checklist include?

An employer benefits compliance checklist covers five groups of tasks: notices to employees, fees paid to the government, annual reports, ACA reporting, and tax-plan paperwork. Which items apply to you depends on your headcount, whether your health plan is insured or self-funded, and whether you run a Section 125 plan.

Use the table below as the master list. Each row is explained in the sections that follow.

When is the Medicare Part D notice due?

The Medicare Part D creditable coverage notice is due before October 15 each year. Plan sponsors that offer prescription drug coverage must tell Medicare-eligible people whether that coverage is creditable or non-creditable (SHRM, 2026).

The notice applies to insured and self-funded plans of any size. It goes to Medicare-eligible active employees, retirees, COBRA participants and their dependents. The rule applies whether your plan pays before or after Medicare.

Employers also report the creditable status to CMS each year. That disclosure is due no more than 60 days after the plan year begins, which is generally March 1 for a calendar-year plan (SHRM, 2026).

Who has to pay the PCORI fee, and when?

Employers that sponsor self-insured health plans owe the PCORI fee, which funds patient-centered outcomes research. The fee is $3.84 per average covered life for plan years ending between October 1, 2025 and September 30, 2026 (Paylocity, 2026).

The fee is due by July 31 of the year after the plan year ends. For a calendar-year 2025 plan, that date was July 31, 2026. The employer files IRS Form 720 and pays the fee based on the average number of covered lives. A fully insured employer does not file this form, because the fee applies to the issuers of those policies.

Does my company have to file Form 5500?

Your company must file Form 5500 for a health and welfare plan if the plan has 100 or more covered participants at the start of the plan year, or if the plan holds assets in a trust. The return is due the last day of the seventh month after the plan year ends. For a calendar-year plan, that is July 31 (The Horton Group).

A small welfare plan with fewer than 100 participants is exempt if it is unfunded, fully insured, or a mix of both. Employees and former employees such as COBRA beneficiaries count toward the 100. Covered dependents do not.

If you need more time, file IRS Form 5558 by the normal due date. That gives a one-time 2.5 month extension.

What are the ACA reporting deadlines for employers?

Applicable large employers must send Form 1095-C to employees and file Forms 1094-C and 1095-C with the IRS every year. For the 2025 reporting year, employers furnished the employee forms by March 2, 2026. The IRS filing deadline was February 28 on paper and March 31 if filed electronically (Parrott Benefit Group, 2026).

The electronic filing threshold is now 10 or more returns in total, not 250. That count combines forms such as W-2s and 1099s. A smaller employer can still be required to file ACA forms electronically.

Missing the offer standards also costs money. For 2026 the ACA employer penalties are $3,340 per full-time employee under Section 4980H(a) and $5,010 under Section 4980H(b) (IRS Revenue Procedure 2025-26).

What does a Section 125 plan need to stay compliant?

A Section 125 cafeteria plan must be a written plan, and the rules in the tax code apply from the first day (26 U.S.C. 125). The written document is the foundation. If you have no plan document, pre-tax payroll deductions for premiums have no tax basis. Our guide to the Section 125 plan document→ shows what the document must say.

The plan must also pass nondiscrimination tests. The tests look at three things:

1. Eligibility. The plan cannot favor highly compensated people, and no employee can be required to wait more than 3 years to join.
2. Contributions and benefits. The plan cannot favor highly compensated participants.
3. Key employee concentration. Key employees cannot receive more than 25 percent of the total qualified benefits (J.J. Keller Compliance Network, summarizing 26 U.S.C. 125).

If a plan fails, highly compensated or key employees lose the tax exclusion for the affected benefits. Small employers can use the simple cafeteria plan safe harbor if they meet its rules. For setup steps, see how to set up a Section 125 plan→.

How much do cafeteria plan payroll savings matter to compliance?

Section 125 deductions reduce taxable wages, so they also change what you report and pay. FICA is 7.65 percent per side: 6.2 percent Social Security and 1.45 percent Medicare. The 2026 Social Security wage base is $184,500 (IRS Tax Topic 751).

That means payroll must code the deductions correctly, and your W-2 reporting must match. If payroll and the plan document disagree, your own records become the audit risk. Review the numbers each January when new limits take effect, such as the 2027 HSA limits→.

What are the other items on the annual calendar?

A few items depend on the benefits you offer:

• ICHRA notice. An employer with an ICHRA must send the notice at least 90 days before the plan year starts. See the ICHRA requirements→.
• Open enrollment materials. Summary documents and notices should go out before enrollment opens.
• Plan document updates. Review the document every year for limit changes and new benefits.
• Records. Keep notices, test results and filing receipts in one folder.

How do I build a calendar from this checklist?

Build the calendar in three steps. First, list your plans and mark each as insured or self-funded. Second, count your covered participants and full-time employees. Third, put the dates from the table above on a shared calendar with an owner and a reminder 30 days before each one.

Many small employers pass this work to a benefits administrator. Benecor Health helps employers set up Section 125 plans and keep the plan document and testing current. You can read the Section 125 cafeteria plan guide→ first, then talk with an expert if you want a second look.

Sources: SHRM, Oct. 15 Deadline Nears for Medicare Part D Coverage Notices (2026); Paylocity, 2026 PCORI Fee Released (2026); The Horton Group, Form 5500 Filing Deadline Is July 31st; Parrott Benefit Group, Upcoming ACA Reporting Deadlines (2026); J.J. Keller Compliance Network, 125 Cafeteria Plans (summarizing 26 U.S.C. 125); IRS Tax Topic 751, Social Security and Medicare Withholding Rates (2026); IRS Revenue Procedure 2025-26.