Special Feature Issue!
As we turn the corner into March and the first signs of spring start to emerge, it’s the perfect time for a reset— clearing out the clutter, getting organized, and setting the stage for a strong season ahead.
In that same spirit, this month’s Benefits Buzz is dedicated to one of the most important (and often underestimated) milestones of the year: Form 5500 filing season.
While it may not have the flash of Open Enrollment, Form 5500 plays a critical role in keeping our clients compliant, protected, and positioned for success. It’s where preparation meets precision—and where the work we do behind the scenes truly makes an impact.
From the Desk of Joe D.
In this special feature issue, our Compliance team walks through everything you need to know: what Form 5500 is, why it matters, key timelines, and how each of us plays a role in ensuring a smooth, accurate filing process.
Whether you’re deeply involved in filings or just looking to strengthen your understanding, this guide is designed to help you feel confident, proactive, and ready for the months ahead.
Let’s take this opportunity to spring forward with clarity, collaboration, and a shared commitment to getting it right.
While there are many elements that contribute to effectively managing an employee benefit plan, few are as critical as compliance. Benefit plans operate within a highly regulated environment at both the federal and state levels, with requirements spanning across areas such as ACA, COBRA, HIPAA, and more. Collectively, these regulations form the foundation upon which plans are designed, administered, and governed, making compliance a central pillar of any successful strategy. At Conner Strong & Buckelew, our commitment to compliance is not simply a requirement—it is a core component of our advisory approach and a key differentiator for our clients. I am incredibly proud of the strength of our compliance team, which I believe is the best in the business. The depth of their expertise, coupled with the guidance and support they provide, is consistently recognized and valued by our clients. As you read this edition of Benefit Buzz, I encourage all of us to remain mindful of the critical role compliance plays in everything we do, and to recognize the outstanding contributions of our compliance team.
Form 5500 Season is Here: What You Need
Form 5500 filing season has officially arrived. And while “Form 5500” may not spark excitement at first glance, make no mistake—this filing sits at the heart of employee benefit plan compliance.
It’s one of the most powerful tools regulators have to ensure benefit plans are run responsibly, transparently, and in the best interests of participants.
Understanding the why, the who, and the when of Form 5500 doesn’t just keep us compliant, it helps us stay proactive, confident, and ahead of potential issues for our clients.
Let’s break it down.
What Is Form 5500—and Why Does It Exist?
Form 5500 is a cornerstone of the federal reporting and disclosure framework under ERISA.
At its core, Form 5500 exists to:
• Confirm that employee benefit plans are operating in compliance with federal standards
• Protect plan participants and beneficiaries through transparency and disclosure
• Provide regulators, Congress, and policymakers with critical data on benefit, tax, and economic trends
In short: Form 5500 is how the government ensures benefit plans are being run responsibly –and how participants’ rights are protected.
What Is ERISA?
ERISA is the federal law that governs most privatesector retirement and health and welfare benefit plans. It establishes clear rules around:
• Reporting and disclosure
• Fiduciary responsibility
• Financial safeguards
• Plan administration and conduct
If a plan is subject to ERISA, compliance isn’t optional – it’s mandatory.
Who Is Responsible for Filing Form 5500?
Responsibility generally falls on the plan administrator. For most single-employer welfare plans, ERISA defines the employer (as plan sponsor) as the plan administrator.
An annual Form 5500 filing is typically required when a plan has 100 or more participants enrolled in any ERISA-covered health or welfare benefit as of the first day of the plan year.
Important reminder: Participants include all enrolled employees – even if they never used the benefit during the year.
Need to Know—and Why It Truly Matters
The Form 5500 Filing Timeline: What You Need to Know
The Form 5500 deadline is tied to the end of the plan year, not the calendar year (unless the plan itself follows a calendar year).
At a Glance
Form 5500 is due seven (7) months after the end of the plan year:
Calendar-year plans (Jan. 1 – Dec. 31):
• Filing deadline: July 31 of the following year
Non-calendar or short plan years:
• Deadline is still seven months after the plan year’s actual end date
This window allows time to gather enrollment data, carrier information, and financial details needed for an accurate filing.
Need More Time? Form 5500 Extensions (Form 5558)
If additional time is needed, an extension may be requested by filing IRS Form 5558 on or before the original due date.
• Provides an automatic 2½-month extension
• For calendar-year plans, this extends the deadline to October 15
Best Practices: Do’s & Don’ts for a Smooth Filing Season
DO: What Keeps Filings Moving
Do confirm plan sponsor details and authorized signer early
Do respond promptly to Compliance questions
Do make confirmations directly on the RFI (in green font)
Do send Schedules as they are received
Do clearly note what’s new or changed
Do save documents in ImageRight under the correct plan year
Do remember Forms 5500 must reflect all benefits offered under the plan, including those not brokered by CSB
DON’T: Common Pitfalls to Avoid
Ꮠ Don’t assume plan sponsor information (including addresses and telephone numbers) are unchanged
Ꮠ Don’t delay responses to Compliance followups
Ꮠ Don’t start new email threads for the same client
Ꮠ Don’t resend documents already submitted
Ꮠ Don’t wait for all Schedules before sending anything
Ꮠ Don’t save documents in the wrong plan year folder
How the Form 5500 Data Collection Process
Understanding the RFI Timeline
Before the RFI Even Arrives
The Compliance Team typically issues the RFI three to four months before the filing deadline. The RFI must be confirmed by the client and collected from insurance carriers based on the plan year.
Because Compliance does not have visibility into carrier changes or contract updates, early communication Team is critical. Sharing known changes before the RFI is released helps avoid unnecessary follow-ups.
Pro tip: Schedule A requests don’t need to wait for the RFI – Account Teams are encouraged to begin
january:
Early Preparation
January sets the tone for a smooth filing season. During this month, Account Teams should:
• Review the prior year (2024) Benefits Guide in ImageRight
• Review the prior year RFI and Schedule A(s)
• Confirm current carriers and benefit offerings
Schedule A(s) should be requested from each applicable carrier for the full plan year. If any benefits are self-billed, request the most recent invoice (typically in December).
february–march:
Data Collection & Review
As Schedule A(s) arrive, begin reviewing them immediately for accuracy and completeness. If items are missing, this is the ideal time to follow up – before deadlines start looming.
march–april:
RFI Review &
Once the Compliance the RFI:
• Review and confirm
• Submit the completed participant counts, available Schedules
• Send materials are ready – don’t everything to
Process Flows:
begin requesting them as early as possible.
march–april:
& Submission
Compliance Team issues confirm the RFI completed RFI, counts, and all Schedules A materials as they don’t wait for to be finalized
april–june:
Drafting the Filing
During this phase:
• Compliance prepares the Form 5500 draft
• Clarifications are requested as needed
• The draft is shared for client review
What Information is Needed to Complete the Form 5500 Filing
• Plan sponsor and administrator details
• Plan name, number, and plan year
• Authorized Signer’s Name and Email Address
• Participant counts
• Complete list of benefits
• Schedule A(s) from carriers
• Self-funded financial data (if applicable)
• Confirmation of changes from prior year
july:
Standard Filing Deadline
Without an extension, client electronic signature is due no later than July 31 july–october:
Extended Filing Period (If Applicable)
With an extension, the client must electronically sign by October 15 outlines all information that communication from the Account follow-ups.
Once approved, Compliance posts the filing and issues electronic signature instructions. If required information remains outstanding as the deadline approaches, consult with your Consultant to determine whether an extension is appropriate.
Behind the Scenes: How a Form 5500
A successful Form 5500 filing is never the result of one person or one moment – it’s a coordinated, multi-step process involving Compliance, Consultants, Account Teams, and the Client.
Understanding who does what, and when, helps keep filings moving smoothly and prevents lastminute scrambles.
Here’s how the Form 5500 process works from start to finish.
Step 1–2: Initiating the Filing
The process begins when the Compliance Team requests confirmation that CSB will be preparing the Form 5500 filing. The Account Team then formally requests that Compliance prepare and submit the filing. This step officially kicks off the filing cycle and ensures Compliance resources are allocated appropriately.
Step 3: Preparing the RFI
Next, Compliance prepares the Request for Information (RFI) - the central document used to confirm plan details and collect all information needed for the filing.
The RFI is then transmitted to the Client-Specific Consultant/Account Team.
Step 4: Working with the Client
The Consultant/Account Team, acting as the primary liaison and works closely with the Client to complete the RFI and Participant Chart.
Responsibilities during this phase include:
• Collecting Schedule A and/or Schedule C when CSB is the Broker of Record
• Coordinating with the client when CSB is not the Broker of Record
• Confirming or identifying changes to:
Vendors and carriers
Coverage offerings
Plan structure
Schedule A or C information
Clear communication during this step is critical, this is where most downstream issues are either avoided or created.
Step 5: Returning Information & Extensions
The Client returns the completed RFI and participant data to the Consultant/Account Team. All final information should be received by Compliance no later than 30 days before the filing due date.
If an extension is needed, Compliance submits Form 5558 to the IRS and confirms acceptance.
Step 6: Consultant Review & Submission to Compliance
The Consultant/Account Team reviews the RFI for completeness and accuracy, confirms all details, and forwards the finalized RFI along with all Schedules to Compliance.
This quality-control step ensures Compliance receives clean, confirmed data.
Filing Comes Together
Step 7: Drafting the Form 5500
Compliance prepares the draft Form 5500 filing. If additional information or corrections are needed, Compliance will request clarification. If no further changes are required, Compliance sends:
• The draft Form 5500
• A cover letter
• DOL EFAST2 electronic signing credential instructions to the Consultant/Account Team for client review and approval.
Step 8–9: Client Review & Approval
The Consultant/Account Team reviews the draft and, if no changes are needed, transmits it to the Client. The Client then:
• Reviews the filing
• Requests any necessary changes or
• Approves the filing for submission to the Department of Labor (DOL)
Step 10–12: Final Authorization & Signature
Once approval is received:
• The Consultant/Account Team notifies Compliance
• Compliance publishes the approved filing in our 5500 software and notifies the Client/Account Team that the filing is published and ready for electronic signature
Step 13–14: DOL Acceptance & Public Posting
After the Form 5500 is signed:
• Compliance transmits the filing to the DOL
• Confirms acceptance
• Notifies the Client and the Consultant/Account Team
• Once accepted, the DOL posts the filing on its website for public viewing. Compliance then notifies both the Client and Account Team of acceptance.
Step 15–17: SAR & Record Retention
With the filing complete, Compliance:
• Prepares the Summary Annual Report (SAR)
• Sends the SAR to the Client and the Consultant/ Account Team
• Saves the Form 5500 and SAR in ImageRight under the appropriate plan year
Why This Process Matters
Every step in this workflow exists for a reason. When roles are clear, timelines are respected, and information flows early and accurately, Form 5500 filings become predictable, compliant, and low-stress – for both internal teams and clients.
Understanding the full lifecycle of a filing doesn’t just make us more efficient, it makes us better advisors.
The Bottom Line
Form 5500 filing season doesn’t have to be stressful – or reactive. Early confirmation, timely communication, and organized documentation make all the difference between a smooth filing and a last-minute scramble.
With strong collaboration and thoughtful preparation, we don’t just deliver compliant filings – we deliver confidence and peace of mind to our clients.
Let’s make this filing season our strongest one yet.
EB Celebrations and Milestones
Congrats to our teammates for their impressive achievements:
• Ava Lopez has completed the required courses for the REBC program
• Brian Weiscarger has completed all courses for the REBC program
• Dania Wade has completed all courses for the REBC program
• Derrick Watkins has completed all courses for the REBC program
• Jagger Teller has completed the elective courses for the REBC program
• Kristin O’Brien has completed the required courses for the REBC program
• Lane Fabiano has received her Group Benefits Associate designation
• Matthew Amadio has completed the elective courses for the REBC program
• Michael Rozier has completed the required courses for the REBC program
• Pete Abitanto has completed all courses for the REBC program
• Peter Moore has received his (EBS I) Health Plan Navigation & (EBS II) Fundamentals in Health Benefits certificates
• Stella Carto has completed all courses for the REBC program
Got news for Benefits Buzz to be posted? From designations to achievements to personal news, send your news and ideas to BenefitsBuzz@connerstrong.com.
