HR compliance can feel like a moving target. Between new regulations, filing requirements, and notice obligations, it’s easy to miss a step. But with the right preparation, you can stay ahead and avoid unnecessary fines or disruptions.
That’s where McConkey comes in. Our 2026 HR Compliance Calendar is designed to help employers keep track of key deadlines throughout the year so you can focus on what matters most, your people.
Start the Year Strong: January through March
January is the perfect time to review your company’s compliance posture and confirm key reporting thresholds for the year ahead.
Begin with critical January determinations:
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Count plan participants as of January 1, 2025: Employers with 100+ participants enrolled in any benefit plan are required to file Form 5500 in 2026.
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Confirm COBRA applicability: Employers must offer COBRA if they had 20 or more employees on more than 50% of business days in the prior year. This determination should also be completed at the start of January.
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Prepare W-2 reporting for medical coverage: Employers must include the total cost of medical plan coverage (employer + employee share) on employee W-2s. These forms are due January 31, 2026.
Additional January housekeeping:
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Confirm all workplace posters, minimum wage, and overtime requirements are current.
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Update your employee handbook and policies to reflect new laws.
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Review leave, training, and pay transparency policies for consistency.
February brings a full slate of IRS and OSHA deadlines:
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Feb. 1: Post OSHA Form 300A summarizing 2025 workplace injuries and illnesses.
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Feb. 2: File and furnish Forms W-2, 1099-NEC, 940, and 941 for 2025.
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Feb. 17: Employees claiming exemption from withholding must submit new Form W-4s.
By March, employers should focus on federal reporting and benefit plan disclosures:
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March 1: Submit Medicare Part D Disclosure to CMS (for calendar-year plans) and 1095-C or 1095-B Forms to employees.
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March 2: Submit OSHA Form 300A electronically and file Form M-1 for MEWAs.
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March 31: File ACA Forms 1094/1095-B or C electronically with the IRS.
Midyear Compliance Milestones
In April, take down your posted OSHA Form 300A by April 30 and file your Q1 Form 941.
By June 1, confirm that your health plan’s Prescription Drug Data Collection (RxDC) report has been submitted to CMS, a task many employers delegate to TPAs or carriers.
July 31 is another major date:
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File Form 941 for Q2.
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Submit and pay PCORI fees (for self-insured plans).
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File Form 5500 for 2025 plan years (calendar-year plans).
Fall Focus: September through November
Fall is crunch time for benefits, notices, and year-end preparation. From September through November, employers should focus on required annual notices and open enrollment readiness.
Required Notices (September–November)
Make sure these core notices are distributed during this period:
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HIPAA Special Enrollment Rights Notice
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Newborns’ and Mothers’ Health Protection Act Notice
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No Surprises Act (NSA) disclosures
September: Prep for Open Enrollment and Benefits Updates
September sets the stage for a smooth open enrollment season.
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Sept. 30: Distribute Summary Annual Reports (SARs) to participants (if Form 5500 was not extended).
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Fully insured employers should also confirm Medical Loss Ratio (MLR) rebates by this date.
Start building your open enrollment communication plan early. Updated materials should include:
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Summary of Benefits and Coverage (SBC)
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CHIP Annual Notice
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WHCRA, COBRA, HIPAA Privacy, and Grandfathered Plan Notices
October: Key Notices and Filing Deadlines
Calendar-year employers face multiple compliance requirements this month:
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Oct. 2: Submit Retiree Drug Subsidy (RDS) program applications.
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Oct. 3: Distribute ICHRA and QSEHRA notices for the 2027 plan year.
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Oct. 14: Send Medicare Part D Creditable Coverage Notices (Creditable/Non-Creditable).
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Oct. 15: File Form 5500 if you received an extension.
November: Final Reminders Before Year-End
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Nov. 2: File Q3 Form 941.
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Remind employees to use remaining FSA, HRA, or PTO balances before expiration or carryover deadlines.
End-of-Year Essentials
As 2026 closes, finalize your compliance checklist:
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Dec. 15: Provide SARs if your Form 5500 deadline was extended.
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Dec. 31: Submit your annual Gag Clause Attestation through CMS, provide any Medical Loss Ratio (MLR) payments to participants, and determine your Applicable Large Employer (ALE) status.
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Confirm annual training, performance reviews, and nondiscrimination testing are complete.
Ongoing Compliance Responsibilities
Some HR and benefits obligations occur year-round and must be addressed consistently, not just during specific months.
Employment Eligibility and New Hire Requirements
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Complete and retain Form I-9s for all new hires within required timelines.
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Provide ACA Marketplace/Exchange Notices to all new employees during onboarding.
COBRA and FMLA Compliance
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Issue COBRA Initial Notices via first-class mail to anyone newly enrolled—such as a spouse added midyear or an employee electing coverage after previously waiving. These must be sent within 90 days of enrollment.
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Follow FMLA notification timelines for eligibility, rights, responsibilities, and designation.
OSHA Reporting and Incident Requirements
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Report severe workplace injuries to OSHA within required timeframes:
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8 hours for fatalities
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24 hours for inpatient hospitalization, amputation, or loss of an eye
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Taxable Benefits & Imputed Income
Confirm accurate taxation on fringe benefits throughout the year.
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Add imputed income for:
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Domestic partner coverage
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Coverage provided to non-tax dependents
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Employer-paid group term life insurance exceeding $50,000 for employees
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All employer-paid spouse or dependent life insurance
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Voluntary life premiums paid pre-tax by employees
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Excise Taxes & Health Plan Violations
If your group health plan has a compliance failure (e.g., late COBRA notice, nondiscrimination failure), file IRS Form 8928 with your corporate tax return to address any applicable excise taxes.
Plan Ahead with McConkey
The most effective compliance strategy is a proactive one. Use McConkey’s 2026 HR Compliance Calendar to stay organized, meet your obligations on time, and reduce risk for your organization.
If you’d like help navigating these deadlines or understanding how they apply to your business, our team is here to support you every step of the way.
