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The Employer Benefits Compliance Calendar: Deadlines You Cannot Miss

ComplianceAugust 7, 2026BeneSkill

Most compliance penalties are not the result of bad faith. They are the result of a date nobody owned.

Benefits compliance failures are rarely dramatic. They are a notice that went out late, a form filed with the wrong code, a document nobody adopted before the plan year started. Each one is small. Collectively they are the most avoidable category of cost in employee benefits.

Here is the recurring calendar most employers with a group health plan are working against. Exact dates vary with your plan year — calendar-year plans are assumed below.

Recurring annual deadlines

DeadlineRequirementWho it applies to
Jan 31Fulfill 1095 statement requests under the alternative furnishing methodALEs and self-insured sponsors
Mar 1Medicare Part D creditable coverage disclosure to CMSAll plans offering Rx coverage
Mar 2Post alternative furnishing notice for prior-year ACA reportingALEs and self-insured sponsors
Mar 31Electronic filing of ACA returns with the IRSALEs and self-insured sponsors
Jul 31PCORI fee payment via Form 720Self-insured and level-funded plans
Jul 31Form 5500 filing (or extension via Form 5558)Plans subject to annual reporting
Sep 30Summary Annual Report distributionPlans filing Form 5500
Oct 15Medicare Part D creditable coverage notice to participantsAll plans offering Rx coverage
Dec 31Gag Clause Prohibition Compliance AttestationAll group health plans

Event-driven obligations

These are not calendar items — they are triggered by something happening, which is precisely why they get missed:

  • COBRA general notice — within 90 days of coverage beginning.
  • COBRA election notice — within 14 days of the plan administrator being notified of a qualifying event.
  • Summary of Material Modifications — 210 days after the plan year in which a change was adopted, but only 60 days if benefits were materially reduced.
  • Mid-year SBC changes — 60 days’ advance notice of any material modification affecting the summary of benefits and coverage.
  • Section 125 plan document — adopted on or before the first day of the plan year. There is no retroactive fix.

Annual and recurring participant notices

  • Summary Plan Description — within 90 days of a participant enrolling, and every 5 years if modified
  • Women’s Health and Cancer Rights Act notice — at enrollment and annually
  • Children’s Health Insurance Program (CHIP) notice — annually
  • Special Enrollment Rights notice — at or before enrollment
  • Notice of Privacy Practices — per HIPAA schedule
  • Patient Protection notice — with the SPD, where applicable

How to actually keep it

  1. Assign an owner for each line. Most misses trace to a deadline that was everyone’s and therefore nobody’s.
  2. Confirm what your carrier or TPA files on your behalf — in writing. Assumed delegation is not delegation, and for self-funded plans the legal responsibility does not transfer at all.
  3. Keep proof of distribution, not just proof of drafting. In an audit, what was sent and when is the question.
  4. Review plan documents before the plan year starts, not when something goes wrong.

If you cannot name who owns the December 31 gag clause attestation at your organization, that is the finding — before any of the filings are even examined.

This article is provided for informational purposes only and does not constitute legal, tax or benefits advice. Requirements vary by plan design, funding arrangement and jurisdiction. Contact BeneSkill to discuss how this applies to your plan.

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