Retirement Plan Compliance: Key Deadlines & Checklist for Employers

Retirement Plan Compliance: Key Deadlines & Checklist for Employers

October 08, 20254 min read

Retirement plans are powerful tools for both employees and employers — for attracting talent, promoting financial security, and building loyalty. But with that power comes responsibility. Missing compliance deadlines can lead to steep fines, legal exposure, and erosion of trust with your workforce.

At Clarity Financial, guiding businesses through clear, confident compliance has always been our mission. Here’s a detailed, year-round compliance guide — with key deadlines, tips, and a checklist — so you stay ahead, avoid penalties, and maintain employee confidence.


Critical Compliance Deadlines: Calendar-by-Calendar Year

January

  • January 31: Provide Form 1099-R to participants who received distributions or rollovers in the prior year. Missing this deadline can trigger IRS penalties per form.

February

  • Mid-February: Begin preparing Form 5500, the annual report/return for your retirement plan. Filing late or inaccurately may result in penalties and audits.

March

  • March 15: File Form 1042-S if your plan distributed amounts to non-U.S. persons. Each missed form can result in IRS fines.

April

  • April 15: Make all employer contributions tied to tax deadlines (such as matching or profit-sharing contributions). Timely contributions are crucial for tax deductions and compliance.

May

  • May 15: Conduct annual nondiscrimination testing (for 401(k) and similar plans). Testing ensures plans don’t unfairly favor highly compensated employees.

July

  • July 31: File Form 5500 if no extension is requested. Late filing triggers escalating penalties from the DOL and IRS.

September

  • September 30: Distribute the Summary Annual Report (SAR) to participants if your Form 5500 was filed on time. This required disclosure ensures transparency.

October

  • October 15: File Form 5500 if you previously filed for an extension. This is the final chance to stay compliant without penalties.

December

  • December 31: Ensure all Required Minimum Distributions (RMDs) are taken by participants aged 73 and older (or the current statutory age). Failing to distribute can result in large excise taxes.


Consequences of Missing Deadlines

Missing any of these deadlines carries risk — not just in money, but trust, reputation, and legal exposure. Some of the costs include:

  • Penalties from the IRS or Department of Labor (DOL) — per form or per day fines.

  • Excise taxes for failure to distribute RMDs properly.

  • Plan disqualification or loss of favorable tax treatment.

  • Employee dissatisfaction, claims, or litigation.

  • Increased audit risk.


Retirement Plan Compliance: Key Deadlines & Checklist for Employers

Tips to Stay on Top of Compliance All Year

To avoid scrambling at the last minute, use these strategies:

  1. Build a compliance calendar.
    Have a shared calendar (digital) that includes all key deadlines. Involve HR, payroll, finance, and your external advisors.

  2. Set early internal milestones.
    For example, start preparation for Form 5500 well before the deadline. Do nondiscrimination testing early so you have time to adjust if needed.

  3. Automate reminders and workflows.
    Use software tools or your benefits/HR platform to set alerts. Ensure payroll, benefits, and finance are aligned.

  4. Regular mid-year check-ins / audits.
    Halfway through the year, review whether plan operations are on track: are contributions timely? Are participant distributions handled properly? Checks help avoid surprises.

  5. Use expert help.
    Third-party administrators (TPAs), ERISA attorneys, or financial advisors (like Clarity Financial) can help interpret legal changes, ensure correct filings, and spot potential compliance problems.

  6. Communicate clearly with service providers.
    If vendors or trustees are involved (recordkeepers, custodians, actuaries), make sure you understand who is responsible for what, which deadlines each one will handle, and track their progress.

  7. Document everything.
    Keep records of filing dates, communications, decisions, amendments, and approvals. Good recordkeeping helps in case of audits or disputes.


Checklist for Employers

Here’s a checklist you can adapt and use in your business:

  • Confirm your plan year and whether any deadlines shift due to non-calendar years.

  • Identify and assign responsibility for each major deadline (HR, payroll, finance, external advisors).

  • Prepare and distribute Form 1099-R to participants needing them.

  • Begin drafting Form 5500 early; verify data, contributions, participant counts.

  • If applicable, file Form 1042-S for non-U.S. distributions.

  • Make all employer contributions that align with tax deadlines.

  • Run nondiscrimination / coverage testing; make corrective actions if necessary.

  • If needed, submit Form 5500 extension request.

  • Distribute Summary Annual Report (SAR) timely.

  • Ensure RMDs for older participants are distributed by year-end.

  • Schedule a mid-year compliance review.

  • Review plan documents, amendments, participant communications to ensure they reflect current law.


Geographic & Legal Considerations to Keep in Mind

Since regulations can vary depending on state or location, it’s especially important for employers in [Florida / Southeastern U.S.] (or wherever you are) to:

  • Check if state laws impose additional deadlines or notices (beyond ERISA).

  • Be aware of local tax filing dates (state taxes) that may influence related deadlines.

  • Understand how state regulatory bodies oversee retirement planning, especially for smaller employers.


Conclusion

Retirement plan compliance is not optional — it’s essential for protecting both your employees and your business. With the right calendar, clear responsibilities, and good external partnerships, you can stay ahead of deadlines, avoid penalties, and build confidence in your benefit offerings.


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Do you want personalized help building or reviewing your retirement plan compliance calendar?

Caroline Raker / Clarity Financial is ready to work with you to:

  • map out all your plan-specific deadlines,

  • model what happens if deadlines shift or requirements change,

  • set up systems and checks so you never miss a deadline,

  • ensure your retirement plan documents and communications stay compliant.

Reach out for a custom compliance audit and deadline strategy session. Let’s make compliance something you don’t have to stress about — only clarity and confidence.

Caroline Raker is a licensed financial advisor and ERISA specialist helping individuals, families, and businesses with retirement planning, insurance, and Social Security strategies. With personal experience managing her parents’ finances, she brings compassion and clarity to every financial decision.

Caroline Raker

Caroline Raker is a licensed financial advisor and ERISA specialist helping individuals, families, and businesses with retirement planning, insurance, and Social Security strategies. With personal experience managing her parents’ finances, she brings compassion and clarity to every financial decision.

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Financial Strategist & Registered Social Security Analyst

Caroline Raker is a trusted financial expert who empowers employers to confidently navigate the complexities of employee retirement services and equips families with proven, strategic insights to secure their financial future—backed by access to 40 leading carriers.

Inspired by her personal experience managing her parents' finances, she became a licensed health and life insurance agent and a Registered Social Security Analyst. With expertise in Social Security optimization, Medicaid, and disability-related financial planning, she is recognized as a trusted resource.

Caroline also volunteers with the Society for Financial Awareness, educating communities on financial literacy. Her mission is to provide personalized financial solutions that secure her clients' futures.

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