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2026 Compliance Deadlines Employers Can’t Afford to Miss

The Enterprise Team· Compliance Advisory January 14, 2026 6 min read

Benefits compliance rarely makes headlines — until a missed deadline turns into a penalty notice. The good news is that nearly every major filing follows a predictable annual rhythm. Mapping those dates now means fewer fire drills later.

The filings that carry the biggest penalties

Not all deadlines are created equal. A handful carry per-employee, per-day penalties that add up quickly for even a mid-sized employer.

  • ACA Forms 1094-C / 1095-C — furnish to employees and file with the IRS on the standard early-year cadence.
  • Form 5500 — due the last day of the seventh month after your plan year ends (with a common July 31 date for calendar-year plans).
  • Medicare Part D creditable-coverage notices — before the October 15 enrollment window.
  • Summary of Benefits and Coverage (SBC) — distributed with open-enrollment materials.

Build the calendar backward from open enrollment

Open enrollment is the anchor for most of your compliance year. Working backward from it — notices, SBCs, non-discrimination testing — keeps requirements from stacking up in the same two weeks.

The employers who stay ahead of compliance treat it as a year-round operating rhythm, not a fourth-quarter scramble.

Want the fully mapped version? Our 2026 Benefits Compliance Calendar lays out every key date month by month — download it free from our homepage.

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Our advisors will review your current benefits program and show you exactly where the opportunities are — no cost, no obligation.

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