The 2026 Benefits Compliance Calendar, Deadline by Deadline

Every January I sit down with our account team and walk the whole year before anything is due. It takes an hour and it saves our clients from the two or three deadlines that always seem to arrive at the worst possible moment. Here is that walk-through, written for a calendar-year plan. If your plan year is different, most of these shift with it, and we can map it for you.

First quarter

February 2 is the W-2 deadline, and if you have 250 or more W-2s you are reporting the aggregate cost of employer-sponsored coverage in Box 12, code DD. March 1 is the Medicare Part D creditable coverage disclosure to CMS. That is the online form, not the employee notice, and it is the one people forget because it has no paper trail. March 2 is when Forms 1095-C have to be furnished to employees, with one important change this year that I wrote about separately: you may be able to post a notice instead of mailing them. March 31 is the electronic filing deadline for the 1094-C and 1095-Cs with the IRS. Almost everyone has to e-file now.

Second quarter

June 1 is the prescription drug data collection report, RxDC, for the 2025 reference year. If you are fully insured, your carrier files it, but expect a request for information in April or May asking for average monthly premium and employer contribution figures. Answer it. If you are self-funded, your TPA and PBM each file a piece and you are responsible for the whole.

Third quarter

July 31 is the big one for self-funded employers. Form 5500 is due for plans with 100 or more participants unless you file the extension to October 15, and the PCORI fee is paid on Form 720 the same day. This year's PCORI rate is $3.84 per covered life for plan years ending between October 1, 2025 and September 30, 2026. September 30 is the Summary Annual Report deadline, two months after the 5500, so it moves if you extended.

Fourth quarter

October 15 is the Medicare Part D notice to employees, which has to go out before the Part D enrollment window opens. For 2026, pay attention to whether your plan is still creditable under the revised test, because the threshold changed. December 31 is the gag clause prohibition compliance attestation. Your carrier or TPA may submit on your behalf, but the plan sponsor is the one on the hook if it does not happen, so get written confirmation.

The two that bite

In my experience the Part D disclosure to CMS on March 1 and the gag clause attestation on December 31 are the ones that slip. Neither generates a form in the mail, neither has an obvious owner, and both are easy to assume someone else handled. Put a name next to each one in January.

This is general guidance, not legal advice, and your plan may have deadlines I have not listed here, especially if you offer an HRA or a non-calendar plan year. If you want a one-page version of this calendar with your plan's actual dates filled in, that is something we build for every client in the first quarter. Just ask.