Compliance is constant. But confusion doesn’t have to be.
HR professionals face a revolving door of tax forms, reporting deadlines, policy updates, and employee notices. All of this comes with different due dates depending on federal, state, or local laws. That’s why building an annual compliance calendar is a must.
In this guide, we’ve mapped out month-by-month compliance touchpoints and ready-to-send employee messages to help you stay compliant while staying ahead of the curve.
Related: Download our 2026 Benefit Comms Calendar Get it here →
January: New Year, No Missed Deadlines
Start the year with clear communication and leave the scrambling to everyone else.
Key Compliance Touchpoints
January 1 – Minimum Wage Updates
Many states and localities update minimum wage or tax limits at the start of the year. Check rates for every jurisdiction where you operate and adjust payroll settings if needed.
January 15 – Q4 Estimated Tax Payment Due
If your organization uses quarterly estimated tax payments for federal taxes, this is a hard deadline. Coordinate with Finance to ensure your filings are complete and on time for payments.
January 15 – Recommended Internal Deadline for Handbook Acknowledgement
After reviewing your employee handbook for updates and compliance, be sure employees have received and acknowledged any changes.
Ongoing: State-Specific Compliance Updates
Many states introduce changes to wage-and-hour laws, harassment training requirements, or new-hire reporting early in the year. It’s crucial you review state labor board guidance for every location where you operate. Flag any updates that apply to your workforce.
Tip for HR:
Build these state-specific updates directly into your HR comms calendar so reminders don’t rely on memory. Centralizing policies and notices makes updates easier to manage and share throughout the year.
Employee-Facing Message Template:
Subject: Happy New Year! A Few Quick HR Reminders.
Hello everyone,
As we begin the new year, here are a few important items to note:
- Minimum wage changes may have taken effect in your location. If this applies to you, please check your pay stub or ask Payroll if you have questions.
- If you received updated handbook policies, please be sure to review them and submit your acknowledgement in .
As always, reach out to with questions.
Best,
Your HR team
February: File It or Fix It
Short month, big responsibilities here. Tax season is upon us, and there are a lot of forms to keep up with.
Key Compliance Touchpoints
February 2 – W-2, 1099 Distribution + Federal Payroll Filings
Because January 31 falls on a weekend in 2026, the federal deadline to issue W-2 and 1099 forms to employees and contractors moves to February 2.
File W-2 Copy A and W-3 with the SSA, Form 1096 with paper 1099s, Form 940 (FUTA) if all deposits have been made, and Form 944 (for small employers if eligible). File your fourth-quarter Form 941 by this date.
February 15 – W-4 Exemption Renewals (Recommended Date)
Employees who claimed exemption from federal tax withholding in 2025 must submit a new Form W-4 for 2026. If not, withholding defaults can occur.
Employee-Facing Message Template:
Subject: W-2 and 1099 Forms and Updates
Hello team,
This is your friendly reminder that your 2025 W-2 and 1099 forms are available or will be sent by February 2. These are important documents you’ll need for tax filing.
Also, if you claimed an exemption on your W-4 last year, please complete a new form so your withholding continues correctly. You can update this in , or reach out to Payroll for help.
Thanks,
Your HR team
March: Health Coverage and Reporting Season
As winter wraps up, March is where tax reporting intersects with benefits and safety reporting. A little clarity goes a long way.
Key Compliance Touchpoints
March 2 – Distribute ACA Forms
If you’re an Applicable Large Employer (50+ full-time equivalent employees), Form 1095-C must be distributed to eligible employees by March 2. If you’re self-insured or a small plan sponsor, Form 1095-B goes to covered individuals.
March 2 – OSHA Electronic Submission
If applicable to your business, submit the OSHA 300A Summary via OSHA’s Injury Tracking Application by this date.
March 15 – Partnership and S-Corp Returns
Form 1065 (Partnerships) and Form 1120-S (S Corps) are due if your organization files on a calendar-year basis.
March 31 – ACA Electronic Filing Deadline
Submit electronic filings for Forms 1094-C/1095-C and 1094-B/1095-B with the IRS by this date.
Employee-Facing Message Template:
Subject: What to Know About Your Health Coverage Tax Form
Hello team,
If you were eligible for health coverage in 2025, your Form 1095-C or Form 1095-B will arrive by March 2. This form reflects your coverage for the year and may be helpful when completing your tax return.
You don’t need to take any action unless a tax preparer asks for it. Just keep it with your records. If you have questions, contact .
Best,
Your HR team
April: Spring Into Compliance
Tax deadlines and safety reporting mean your April checklist should be anything but passive.
Key Compliance Touchpoints
April 1-30 – OSHA Form 300A Posting (ongoing)
Continue posting your OSHA 300A summary in a visible location until April 30. This is a requirement for most employers covered by OSHA recordkeeping rules.
April 15 – Q1 Estimate Tax Payments Due
If your business pays quarterly estimated taxes, the first installment for 2026 is due.
April 30 – Q1 Form 941 Filing Deadline
Employers must file Form 941 to report income taxes, Social Security tax, or Medicare tax withheld from employee paychecks for Q1 2026.
Employee-Facing Message Template:
Subject: Q1 Compliance Reminders + What’s Ahead
Hey team,
As we wrap up Q1, a few compliance items are in motion behind the scenes:
- We’re filing federal tax reports (you don’t need to do anything).
- Our OSHA safety summary remains posted until April 30. Feel free to take a look.
If you have questions about workplace safety policies, tax forms, or anything else HR-related, we’re just a message away.
Best,
Your HR team
May: Benefits, Breaks, and a Mid-Year Check
May is a great time to assess benefits understanding and prep for the mid-year stretch.
Key Compliance Touchpoints
Mid-May – Mental Health Awareness (optional but encouraged)
While not a regulatory requirement, many HR teams use this time to share resources about EAPs, wellness benefits, and burnout prevention. It’s a good moment to engage employees around benefits that often go unused.
May 31 – Deadline for 401(k) ADP/ACP Corrections (Non-EACA Plans)
If your plan failed nondiscrimination testing for the previous year, you must make corrections by the end of May to avoid penalties.
Employee-Facing Message Template:
Subject: Wellness Resources You Might’ve Missed
Hello team,
May is Mental Health Awareness Month, and we want to make sure you know what’s available to you:
- Our Employee Assistance Program (EAP) offers free, confidential support.
- You also have access to , depending on your benefits elections.
You don’t need to be in crisis to reach out. Sometimes a quick chat can make a big difference.
Take care,
Your HR team
June: Midpoint Check-ins
Halfway through the year, June is all about check-ins on DEI, performance, and summer policy reminders.
Key Compliance Touchpoints
June – Mid-Year Performance Check-ins
While not federally required, many organizations schedule mid-year reviews in June to support employee development and keep goals aligned. It’s also a good opportunity to re-share expectations and recognition programs.
Employee-Facing Message Template:
Subject: Let’s Check In, Performance + Planning
Hi team,
We’re halfway through 2026 (yes, already). To help you stay aligned and supported, we’re kicking off mid-year performance check-ins.
Managers will be scheduling quick conversations. These are future-focused meetings. We’ll use this time to remind you of professional development tools and our recognition program.
No paperwork to prep. Just show up ready to share how things are going.
Best,
Your HR team
July: New Laws, New Pay Rates, and Summer Safety
Summer heat isn’t the only thing rising. New mid-year wage updates and safety obligations are here.
Key Compliance Touchpoints
July 1 – State and Local Minimum Wage Adjustments
Many states and cities update minimum wage rates mid-year. Double-check any jurisdictions where your employees are located.
July – Mid-Year Safety Refresh
While not tied to a federal deadline and distinct from earlier OSHA reporting requirements, July is a smart time to review safety protocols. If you have frontline workers or employees in the field, you can touch on heat-related illness prevention.
July 31 – Form 5500 Deadline for Calendar-Year Plans
For calendar-year retirement or welfare benefit plans, July 31 is the deadline to file Form 5500, which reports plan information to the IRS and Department of Labor. (Extensions may be available if requested.)
Employee-Facing Message Template:
Subject: Summer Pay + Safety Reminders
Hi team,
A few mid-year updates:
- Minimum wage changes take effect in some states on July 1. If your rate is affected, you’ll see it reflected in your next paycheck.
- It’s also a good time to review safety procedures, especially for those working outdoors or in higher-risk areas.
If you have questions about pay, schedules, or safety resources, HR is here to help.
Best,
Your HR team
August: Prep Now, Stress Later
August is your launchpad for fall campaigns like open enrollment and handbook updates.
Key Compliance Touchpoints
August – Begin Open Enrollment Prep
You’re not required to launch OE yet, but if you start prepping now, your fall timeline won’t feel so rushed.
August – Review Employee Classifications
Now is a good time to audit employee classifications to ensure FLSA compliance before annual reviews and compensation changes.
Employee-Facing Message Template:
Subject: We’re Gearing Up for Open Enrollment
Hi team,
Open enrollment is coming up this fall, and we’re getting things ready early so it’s easier for you.
This month, you’ll start to see some resources on what’s changing (and what’s staying the same) with our benefits.
As always, feel free to reach out with questions. More info coming soon.
Best,
Your HR team
September: Training, Policies, and the Calm Before OE
Compliance training and handbook updates take center stage as we head into Q4.
Key Compliance Touchpoints
September – Required Training Refreshers (varies by state)
Many states require completion of annual anti-harassment or safety training by year’s end. September is an optimal time to do this before Q4 gets too full.
September – Employee Handbook + Policy Review
Start reviewing and drafting updates to your employee handbook, especially if you’ve made changes to remote work policies, DEI initiatives, or time-off structures.
Employee-Facing Message Template:
Subject: Your Annual Training + What’s Coming Next
Hi team,
Heads up: Annual compliance training is launching this month. You’ll receive assigned modules .
We’re also reviewing our employee handbook to reflect updates around . Once finalized, we’ll send a summary your way.
Thanks in advance for your attention to the training.
Best,
Your HR team
October: The Calm Before the Compliance Storm
Open enrollment is about to launch, but don’t forget your Medicare Part D notices.
Key Compliance Touchpoints
October 15 – Medicare Part D Notice Deadlines
Employers offering prescription drug coverage must provide the annual Medicare Part D notice to Medicare-eligible employees before October 15. This helps them decide if they need supplemental coverage.
October – Final Open Enrollment Prep
Confirm your open enrollment dates, finalize plan documents, and schedule employee education campaigns across channels.
Employee-Facing Message Template:
Subject: Prescription Drug Coverage: What You Need to Know
Hi team,
If you’re eligible for Medicare (or have a family member who is), you’ll receive a notice from us about how our prescription coverage compares to Medicare Part D.
You don’t need to do anything right now. This just gives you info to help you decide what works best for your situation.
Questions? Our HR team is happy to walk you through it.
Best,
Your HR team
November: Open Enrollment and Year-End in Sight
This is your moment. Clear communication now saves a world of questions later.
Key Compliance Touchpoints
November – Launch Open Enrollment
Most companies run OE in November. Ensure all employees have access to plan information, decision-support tools, and enrollment deadlines. Use multiple formats: email, SMS, chatbots, manager huddles, intranet pages, and digital postcards.
November – Begin Year-End Payroll Review
Start reviewing pay data, W-2 details, and benefits decisions to catch errors early. Doing this sets you up for a much smoother January.
Employee-Facing Message Template:
Subject: It’s Time to Choose Your 2026 Benefits
Hi team,
Open Enrollment starts this week!
You’ll find everything you need in one spot:
✔️ Plan options
✔️ What’s new or changing
✔️ A deadline (don’t miss it!)
We know benefits can be confusing, so we’re keeping things simple. Let us know if you have questions.
Best,
Your HR team
December: Wrap-Up Mode Activated
Make your year-end checklist, and check it twice.
Key Compliance Touchpoints
December – Finalize Year-End Filings
Review employee records, update contact information, and confirm payroll data for W-2 and Form 1095-C.
December – Confirm ACA Reporting Readiness
If you’re an Applicable Large Employer (ALE), confirm that you’ve tracked health coverage for eligible employees to prepare for January filings.
December – PTO + Carryover Notices
Notify employees about any PTO balances that will expire, roll over, or be paid out by year’s end. Check your state laws to see if these are required.
Employee-Facing Message Template:
Subject: Year-End Wrap-Up + What to Know
Hi team,
As we head into the holidays, here are a few things to check off your list:
- Review your pay + benefits info. Doing this ensures your W-2 is accurate.
- Check your PTO balance. Some plans have a “use it or lose it” rule.
- Confirm your contact info. Make sure tax documents go to the right place.
Reach out with any questions. We’re here to help you wrap up the year right.
Best,
Your HR team
Keep it Proactive, Predictable, and a Lot Less Painful
You don’t need a 20-tab spreadsheet or an alphabet soup of acronyms to stay compliant. You need a plan to stay consistent, clear, and tied to what employees actually need to know.
Building your communications calendar now sets the tone for the rest of the year. It reduces last-minute scrambles, prevents costly oversights, and helps HR look less like the department of deadlines and more like the team that’s always one step ahead.
Compliance may be non-negotiable. But how you communicate it is where you really shine.