2026 Health & Welfare Plan Compliance Calendar: Key HR Deadlines for MD, DC, and VA Employers

This compliance calendar highlights key federal deadlines and best practices for group health plans throughout 2026. Some obligations are tied to dates, while others are ongoing or triggered by specific events.

Maintaining a calendar can help your organization plan, coordinate responsibilities with carriers and third-party administrators, and meet compliance requirements.

Key Compliance Deadlines

Staying ahead of compliance deadlines is crucial. Let’s dive into the key months and what each requires from your team.

January:

Jan. 1: Transparency in coverage (TIC) regulations require group health plans to make self-service price comparison data available online. Plan members should be able to get an estimate of their cost-sharing amounts for all plan items and services.

Jan. 1: According to TIC guidance, self-funded health plans are required to publish the necessary machine-readable files. These files must report:

• In-network rates and

• Out-of-network allowed amounts and billed charges

Machine-readable files must be made available on a public site and updated monthly.

Jan. 31: Note: Because Jan. 31 falls on a Saturday in 2026, deadlines for Forms W-2 and W-3 have been pushed to Feb. 2. See below.

February:

Feb. 2: Distribute Form W-2 to employees. W-2 forms must report the aggregate cost of employer-sponsored health coverage.

Feb. 2: File Forms W-2 and W-3 with the Social Security Administration. The tax assistance company Zenwork recommends electronically filing W-2 forms by Jan. 25. The extra time provides a cushion to review and correct errors before the Feb. 2 deadline.

Feb. 16: Update your plan’s Notice of Privacy Practices and Health Insurance Portability and Accountability Act (HIPAA) privacy policies to comply with new federal confidentiality rules for substance use disorder (SUD) records (compliance is required two years after the Final Rule’s publication in the Federal Register, which took place on Feb. 16, 2024). Spell out when and how SUD information can be disclosed, and train HR staff accordingly.

March:

March 1: Submit the Medicare Part D Creditable Coverage Disclosure to the Centers for Medicare and Medicaid Services (CMS). This disclosure informs Medicare-eligible plan participants whether your group drug plan is as good as or better than Medicare Part D coverage. The submission deadline is 60 days after the start of the plan year, which is March 1 for calendar-year plans.

March 2: Applicable large employers (ALEs) are organizations with 50 or more full-time equivalent employees. ALEs must post or provide Affordable Care Act (ACA) statements to employees. One way to comply is to ensure that a clear and concise notice of ACA Form 1095-C appears online by March 2. The notice must tell employees about the availability of Form 1095-C. It must remain posted through Oct. 15.

March 2: ALEs that don’t provide a notice of Form 1095-C must automatically distribute these statements to employees by this date.

March 2: Non-ALEs with self-insured plans must ensure that a clear and concise notice of ACA Form 1095-B appears online. The notice tells employees about the availability of Form 1095-B. It must remain posted through Oct. 15.

March 2: Non-ALEs that don’t provide a notice of Form 1095-B must automatically distribute these statements to employees by this date.

March 15: If your flexible spending account (FSA) program offers a 2½-month grace period, March 15 is the deadline for FSA participants to use funds from the previous year. Unused FSA funds will be forfeited.

March 31: ALEs must report health plan coverage information by filing Forms 1094-C and 1095-C with the IRS. You can request a 30-day extension by filing Form 8809.

March 31: Non-ALEs with self-insured plans must file forms 1094-B and 1095-B with the IRS. You can request a 30-day extension by filing Form 8809.

April:

Use this time to review processes related to ongoing plan responsibilities and Employee Retirement Income Security Act (ERISA) requirements. Examples include:

• Children’s Health Insurance Program Reauthorization Act (CHIPRA) notices

• Consolidated Omnibus Budget Reconciliation Act (COBRA) notices: Election, qualifying events, continuation coverage rights, early termination, insufficient payment, etc.

• Health Insurance Portability and Accountability Act (HIPAA) notices: Special enrollment rights, privacy practices, breach notification, etc.

• Mental Health Parity and Addiction Equity Act (MHPAEA) notices: Medically necessary determination criteria, claims denial, increased cost exemption, etc.

• Newborns’ and Mothers’ Health Protection Act Notice

• No Surprises Act disclosures

• Women’s Health and Cancer Rights Act (WHCRA) notices

Ensure that notices are up to date and distributed promptly when a triggering event occurs. Document your procedures and retention practices. These actions aren’t tied to a specific calendar date, but they are vital to maintaining plan compliance.

May:

May is a good month to review ongoing plan governance. These efforts protect plan participants, strengthen fiduciary oversight, and allow for corrective actions to be taken before open enrollment and year-end deadlines.

• Work with vendors to ensure ongoing compliance. In particular, review transparency in coverage and Consolidated Appropriations Act requirements to improve benefits transparency and participant protection. Verify that the required price comparison tool is functional. Update machine-readable files. Prepare for the annual Gag Clause Prohibition Compliance Attestation, due at the end of the calendar year.

• Review plan documentation and notices. Ensure that plans include an up-to-date summary plan description, summary of benefits and coverage, and summary of material modifications. Check that they have been distributed on time and in accordance with required schedules. Verify that notices are sent for triggering events related to COBRA, HIPAA, CHIPRA, WHCRA and other legislative requirements.

• Examine claims and appeals procedures. Confirm that ERISA notices and timelines are being followed. Review adverse benefit determination letters for clarity and compliance.

• Assess HIPAA privacy and security. Review business associate agreements to ensure proper handling of protected health information. Ask vendors for evidence of security audits and breach response protocols.

• Consider eligibility audits. Verifying benefits and dependent eligibility can reduce risks and costs for current and future plan years.

• Document vendor performance. Review costs, services and return on investment. Ensure that fees and solutions meet fiduciary obligations.

• Prepare for open enrollment. Discuss potential plan design changes, draft updates to plan documents, and confirm timelines with carriers and third-party administrators.

June:

June can help you build momentum toward significant Q3 deadlines. Laying the groundwork now helps avoid last-minute issues and potential penalties.

June 1: Submit the Prescription Drug Data Collection (RxDC) report to the CMS. This report includes prior-year data on drug spending, rebates and premiums for calendar-year plans. The Horton Group insurance company recommends working with vendors before this date to ensure complete and accurate submissions.

Prepare for July 31 deadlines: Two important deadlines fall at the end of July:

• Form 5500 filing for calendar-year plans

• Patient-Centered Outcomes Research Institute (PCORI) fee payment for self-funded plans

Use the remaining time in June to gather claims data, review plan financials, and coordinate responsibilities with vendors.

July:

July 31: File IRS Form 720 to pay the annual PCORI fee. The PCORI fee funds research into health care choices, treatments and decisions. The IRS updates the fee amount annually. The fee is due by July 31 following the end of the plan year. Insurance carriers pay the PCORI fee on behalf of fully funded plans. If your organization administers a self-funded plan, you are responsible for calculating, reporting and paying the PCORI fee. Use Form 720 to make the PCORI payment.

July 31: File Form 5500. Form 5500 provides information on your plan’s operations, investments and financial standing. You must file Form 5500 annually if your health and welfare plan holds its assets in a trust or has 100 participants or more at the beginning of the plan year. Use the Employee Retirement Income Security Act (ERISA) Filing Acceptance System (EFAST2) to file your form.

July 31: File Form 5558 to receive an automatic extension on filing Form 5500. Filing Form 5558 extends the deadline for Form 5500 by 2½ months, setting the new deadline at Oct. 15.

August:

There are no major federal deadlines in August. This is a good month to review plan documentation and prepare for open enrollment.

Review your plan design for any changes that may require updated notices, such as in a summary plan description or a summary of material modifications.

The benefits and HR consulting company Bolton recommends including annual notices in open enrollment paperwork. Doing so can help reduce costs and administrative burdens.

ACA regulations require plans to provide a summary of benefits and coverage (SBC) to plan participants during open enrollment. The Department of Labor offers a template and rules for SBCs.

September:

Sept. 30: Distribute a Form 5500 summary annual report (SAR) to participants and beneficiaries. Plans that file Form 5500 must provide a SAR that summarizes the information in Form 5500. The SAR is due nine months after the end of the plan year, or two months after the Form 5500 deadline. The Form 5500 deadline is July 31, making the SAR deadline Sept. 30. If your organization filed Form 5558 for an automatic extension of 2½ months to file Form 5500 (creating a new deadline of Oct. 15), the SAR would be due by Dec. 15.

Sept. 30: Look for medical loss ratio (MLR) rebates. The ACA requires insurance issuers to spend 80% to 85% of their premiums on patient care and quality improvements. If they don’t meet the minimum MLR, they must provide plan sponsors with a rebate by the end of the MLR reporting year, which is Sept. 30. Rebates that qualify as plan assets under ERISA must be used to improve benefits for plan participants. In general, these rebates should be distributed within three months of receipt.

October:

Oct. 3: If you offer an individual coverage health reimbursement arrangement (ICHRA), provide eligible employees with a notice for 2027. The ICHRA notice must be sent at least 90 days before the start of the plan year. For calendar-year plans, Oct. 3 is the deadline for the 2027 plan year.

HealthCare.gov reports that the notice must include:

• Start and end dates for coverage

• Reimbursement amounts

• Whether the ICHRA offer extends to dependents

Oct. 3: If you offer a qualified small employer health reimbursement arrangement (QSEHRA), provide eligible employees with a notice for 2027. The QSEHRA notice must be sent at least 90 days before the start of the plan year. For calendar-year plans, Oct. 3 is the deadline for the 2027 plan year.

The IRS reports that the notice must include the following:

• The eligible employee’s permitted benefit amount for the year

• A statement notifying eligible employees that they must inform their chosen health insurance exchange of their permitted benefit amount if they receive advance premium tax credits

• A statement notifying eligible employees that they could be liable for a tax penalty if they lack minimum essential coverage (MEC) and that reimbursements for months without MEC could become taxable income

Oct. 14: Distribute Medicare Part D notices. Group health plans that offer prescription drug coverage must provide a notice to employees who are eligible for Medicare Part D. The notice must tell them whether the plan provides “creditable coverage” that is as good as or better than Medicare Part D coverage. The CMS offers creditable coverage model notice letters.

Oct. 15: If you used Form 5558 to extend the filing deadline for Form 5500 from July 31 to Oct. 15, the deadline has arrived. Form 5500 provides information on your plan’s operations, investments and financial standing. You must file Form 5500 annually if your health and welfare plan holds its assets in a trust or has 100 participants or more at the beginning of the plan year. Use the Employee Retirement Income Security Act (ERISA) Filing Acceptance System (EFAST2) to file your form.

November:

There are no major federal deadlines in November. This is a good month to review plan documentation and communications.

Confirm that all open enrollment notices have been properly distributed. Examples could include:

• Summary of benefits and coverage

• Summary plan description and summary of material modifications, if plan design changes occur

• Women’s Health and Cancer Rights Act (WHCRA) notice

• Children’s Health Insurance Program (CHIP) notice

• Health Insurance Portability and Accountability Act (HIPAA) notices

• Medicare Part D creditable coverage notice

Combining annual notices with open enrollment can meet legislative requirements and reduce costs.

Remind employees to review their FSA balances and deadlines. FSAs have a use-it-or-lose-it rule. This means that participants forfeit any funds not spent by the end of the plan year. Your FSA plan can offer a 2½-month grace period or a rollover option with an IRS-set amount each year; it cannot offer both. If you don’t offer a grace period or a rollover option, FSA funds must be spent by Dec. 31 for calendar-year plans.

December:

Dec. 15: If you extended the deadline for filing Form 5500 from July 31 to Oct. 15, it is now time to distribute the Form 5500 summary annual report (SAR) to participants and beneficiaries. Plans that file Form 5500 must provide a SAR that summarizes the information in Form 5500.

Dec. 31: Submit a Gag Clause Prohibition Compliance Attestation. The Consolidated Appropriations Act requires health plans and insurers to confirm that their plan contracts don’t contain gag clauses blocking the release of cost and quality data. It’s part of an effort to increase health care transparency. Fully insured health plans can have their carriers provide the attestation on their behalf. Employers with self-insured health plans can have a third-party administrator submit the gag clause attestation. However, the responsibility ultimately lies with the employer. Whether fully or self-insured, review your contracts and confirm that the gag clause attestation will be submitted by Dec. 31.

Dec. 31: This is the year-end spending deadline for calendar-year FSAs. Unless your plan offers a rollover option or grace period, FSA participants must spend any remaining amounts by Dec. 31 to avoid forfeiting funds.

Put your calendar to work

This calendar can help keep you on track and in compliance throughout the year. As you map out timelines, work with your benefits partners to prioritize tasks and align responsibilities.

For more information, contact your insurance broker or benefits adviser. They can provide plan-specific guidance and strategies for 2026 and beyond.

Note: This calendar provides general information to support your compliance efforts. This information is not comprehensive and should not be considered legal advice. Requirements can vary by plan design, plan year and funding arrangement. Work with your benefits adviser and legal counsel to identify specific plan needs.