A Year-Round Benefits Compliance Calendar You Can Use

Why benefits deadlines slip

Benefits compliance rarely fails because an employer doesn't care. It fails because the deadlines are scattered across agencies, vendors and plan years, and nobody owns the whole picture. A notice goes out late or a form gets skipped, and you find out during an audit or when an employee asks a question you can't answer.

A calendar fixes that. This guide groups the common recurring items by season so you can drop them into a shared calendar with a named owner for each. Your plan types, company size and plan year will change the details, so treat this as a map, not a legal checklist.

One note before we start. Many dates depend on your plan year. If your plan year isn't the calendar year, shift the items below to match, and confirm exact dates with a licensed advisor or benefits counsel.

Fall: notices that go out around open enrollment

Fall is the busiest stretch because several requirements are tied to enrollment season. Most of these are easy to do and expensive to forget.

• Medicare Part D creditable coverage notice: if your health plan includes prescription drug coverage, Medicare-eligible people must be told whether it is considered creditable. This generally needs to reach them before the Medicare enrollment period opens in the fall.
• Summary of Benefits and Coverage: group health plans must provide plain-language summaries at enrollment and renewal. Your carrier or administrator usually produces them, but making sure employees actually receive them is often your job.
• Safe harbor 401(k) notice: if your retirement plan uses a safe harbor design, the annual notice is generally due ahead of the new plan year.
• Annual federal health plan items: group health plans have transparency requirements, such as an attestation about certain contract terms and prescription drug data reporting. Fully insured employers often rely on the carrier for these, so get written confirmation of who is handling them.

Winter: year-start forms and updated limits

The new year brings reporting for the year just ended and new figures for the year ahead. Put these on the calendar before the holidays so they don't collide with payroll year-end.

• ACA reporting: if you are an applicable large employer (generally 50 or more full-time equivalent employees, with 30 hours a week counting as full-time), you furnish coverage statements to employees and file with the IRS. Employee statements are due early in the year and IRS filings later in the spring. Check the current dates and any extensions each year.
• Updated limits: HSA, FSA, commuter and retirement contribution limits, along with the ACA affordability threshold, are set each year. Look up the current figures and update your payroll settings and employee materials.
• Payroll alignment: confirm that deductions match elections and that benefits are coded correctly for tax reporting. Ask your payroll provider or tax professional how to handle each benefit.
• Annual notices: depending on your plans, this is a good time to send the children's health coverage premium assistance notice, the Women's Health and Cancer Rights Act notice and your HIPAA privacy notice.

Spring and summer: plan filings and testing

Once the year-start rush passes, the work shifts to plan-level filings and checks. These tasks are less visible to employees, but they matter if a regulator or auditor ever looks.

• Form 5500: most retirement plans and many group health plans must file an annual return. It is generally due by the end of the seventh month after the plan year ends, and an extension is available. Some small plans have exceptions, so confirm yours.
• Summary Annual Report: when a plan files a Form 5500, participants in many plans must receive a summary of it. Add this to the same calendar entry as the filing.
• Nondiscrimination testing: 401(k) plans and Section 125 cafeteria plans are tested to confirm they don't favor highly paid employees. Early results leave time to correct problems.
• Retirement plan review: confirm contributions were deposited on time, review investment options and fees, and keep notes on your decisions.
• CalSavers: if you don't offer a qualifying retirement plan, confirm your registration and ongoing obligations with the program.
• Eligibility audit: check hours for variable-hour employees, waiting periods and dependent eligibility. A mid-year check catches errors before they build up.

Triggered deadlines that never land on a calendar

Some of the most costly deadlines start with an event, not a date. You can't schedule them, but you can build a routine so they get handled the same way every time.

Think of five common triggers. A new hire joins, and enrollment materials and required notices have to go out within the time the law sets. An employee has a qualifying life event, such as marriage, a birth or loss of other coverage, and a limited window opens to change elections. Someone leaves or loses eligibility, and COBRA or Cal-COBRA notices start a strict clock. An employee goes on a protected leave, and you have to think through benefit continuation and notices under California and federal leave rules. You make a material plan change, and employees may need advance notice or an updated summary.

A simple trigger log helps. Record the event, the date, which notice went out, who sent it and how. When the same person handles each trigger the same way, errors drop and proof of delivery is already in your files.

Next steps you can take this month

You don't need special software to start. A shared spreadsheet and a few honest conversations will get you most of the way there.

• List every benefit plan you sponsor, with its plan year dates and plan documents.
• Build a grid with five columns: the notice or filing, the due date, the owner, whether a vendor or your team handles it, and where proof of delivery is stored.
• Ask your carrier, administrator, payroll provider and retirement plan recordkeeper for a written list of what they handle and what stays with you.
• Enter each date in a shared calendar with reminders well ahead of the deadline, and name a backup for each owner.
• Create a compliance folder with copies of notices, distribution logs and acknowledgments. If your team is bilingual, consider delivering notices in the language employees read most comfortably.
• If you'd like a second set of eyes, a benefits review with an advisor is one way to find gaps in the grid.

This article is general education for employers, not legal, tax or plan advice. Benefit rules and options depend on your group size, location and plan, so talk with a licensed advisor before making changes. Sixth Man Employer & Insurance Services, CA Insurance License #0I01929.