Form 5500 is the annual report for employee benefit plans. Plenty of employers have never filed one and are entirely correct not to. Plenty of others should be filing and are not.
The deadline
Form 5500 is due by the last day of the seventh month following the end of the plan year. For a calendar-year plan, that is July 31 of the following year.
If your plan year is not the calendar year, count seven months from your plan year end. A July 1 plan year ends June 30, which puts the filing due January 31.
The extension
File IRS Form 5558 on or before the normal due date and you get an automatic 2.5-month extension. For a calendar-year plan that moves the deadline to October 15.
The extension is automatic if you file the request on time. It is not available after the fact — miss July 31 without having filed the 5558, and you are simply late.
The exemption
A welfare benefit plan is exempt from filing if both of these are true:
- It had fewer than 100 covered participants at the beginning of the plan year, and
- It is unfunded or fully insured. A combination of insured and unfunded benefits still qualifies.
Both conditions have to hold. A fully insured plan with 140 participants files, because it fails the first. A plan with only 40 participants still files if it is neither unfunded nor fully insured, because it fails the second.
Who counts as a participant
This is where employers miscount, usually in their own disfavor.
Covered dependents do not count. Employees and former employees do — including COBRA beneficiaries.
So a plan covering 80 employees and 120 dependents has 80 participants, not 200. But a plan covering 95 employees plus 8 COBRA beneficiaries has 103, and it files.
Count at the beginning of the plan year, not at the end and not today.
If you have never filed and think you should have
The Department of Labor operates a voluntary correction program for delinquent filers with substantially reduced penalties compared to being found out. Talk to your benefits counsel before filing a late return cold — the order of operations matters.
Source: Form 5500 deadline, extension, and small plan exemption as summarized by Leavitt Group
Verified against primary sources in August 2026. Deadlines and thresholds change — confirm against current IRS and DOL guidance, or call us at (920) 243-4006 and we will check it with you.
This is the work we do.
Benefi administers group benefit plans for employers — including the deadlines above. If you are not certain where your plan stands, that is a short conversation, not a project.