If your company’s benefits plan renews on January 1, the next ten weeks matter more than almost any other stretch of the HR calendar. Open enrollment is when employees make decisions that affect their health coverage, their paychecks, and often their sense of whether the company has their back. For small employers with 20 to 200 employees, it’s also a compressed window with real compliance deadlines attached, which makes it easy to leave something undone. Here’s a practical look at what needs to happen, and when, so enrollment goes smoothly instead of becoming a scramble in December.
Why the Calendar Matters More Than It Seems
Employer-sponsored open enrollment isn’t governed by the same window as the ACA individual marketplace, but the two calendars overlap in a way that creates confusion for employees. Marketplace open enrollment for 2027 coverage runs from November 1, 2026 through January 15, 2027 in most states, with December 15 as the deadline to lock in a January 1 start date. Group plans, by contrast, run on whatever schedule the employer and carrier set, and most companies with a calendar-year plan hold their enrollment window in October or November so elections can be processed in time for January 1 effective dates. If your open enrollment period bleeds into late December, you’re cutting it close with carriers and payroll systems that need lead time to load elections correctly.
A good rule of thumb: work backward from your effective date. If coverage needs to start January 1, enrollment should close by early-to-mid December at the latest, which means it should open by early-to-mid November, which means renewal decisions and plan documents need to be finalized by October. Waiting until November to start thinking about renewal terms is the single most common reason small employers end up rushing communications, shortchanging employee questions, or missing a compliance notice altogether.
The Notices You’re Required to Send
Open enrollment isn’t just a benefits election period, it’s also when several federal notice requirements come due, and missing them creates real exposure even for a small, well-intentioned employer.
The Medicare Part D Notice of Creditable Coverage is the one with a hard, unmovable deadline: it must go out annually by October 15, regardless of when your plan year starts or when your enrollment window opens. This notice tells Medicare-eligible employees, dependents, and COBRA participants whether your prescription drug coverage is at least as good as Medicare Part D, which affects whether they’ll owe a late-enrollment penalty if they delay Medicare enrollment later. Because the October 15 deadline is fixed, it’s worth sending regardless of your own enrollment timing.
You’re also expected to distribute a CHIP notice annually, informing employees that they or their dependents may qualify for premium assistance through Medicaid or their state’s Children’s Health Insurance Program, and to make sure every enrollee gets a current Summary of Benefits and Coverage (SBC) with the year’s plan details. For insured plans, your carrier typically prepares the SBC, but distributing it to employees is still the employer’s job. If anything about your plan design is changing for the new year, that also needs to be communicated through an updated Summary Plan Description or a Summary of Material Modifications, not just a passing mention in an enrollment email.
What to Actually Walk Employees Through
Beyond the compliance paperwork, open enrollment is a communication exercise, and it’s worth treating it that way rather than just forwarding a benefits guide and a deadline. Employees are, on average, not fluent in insurance terminology, and the plans and account options available to them keep shifting year to year. This year is a good example: HSA contribution limits are rising to $4,400 for self-only coverage and $8,750 for family coverage in 2026, with an additional $1,000 catch-up allowed for employees 55 and older. Health FSA limits are increasing to $3,400, with a maximum carryover of $680 for plans that allow it. Dependent Care FSA limits saw a bigger jump this year, up to $7,500 for most filers, a change enacted through recent federal legislation and the first increase to that limit since 1986. If your plan offers any of these accounts, walking employees through what changed, and what it means for their paycheck deductions, is worth a few minutes in your enrollment materials or a short info session.
It’s also worth being explicit about what happens if someone does nothing. Some plans default non-responders into current elections, others require an active choice every year, or drop coverage entirely if no election is made. Whatever your plan’s rule is, state it plainly and more than once, because “I didn’t realize I had to re-enroll” is one of the most common and most avoidable enrollment complaints.
Give Yourself Room for Questions
The employers who have the smoothest enrollment periods tend to build in time for one-on-one or small-group questions, not just a static packet of documents. That doesn’t need to be elaborate. A single scheduled call with your broker or a short office-hours block where an HR lead can field plan comparison questions goes a long way toward reducing confused or incomplete elections, which in turn reduces the number of mid-year “I picked the wrong plan” conversations that are much harder to fix once the window has closed.
If you haven’t started renewal conversations with your broker or carrier yet, now is the moment. Confirm your plan year’s effective date, get final rates and any plan design changes in writing, and set your internal enrollment window with enough runway before your October 15 Medicare Part D deadline and your carrier’s own election cutoff. Enrollment season rewards employers who start early far more than it punishes anyone for asking questions late, so err on the side of getting ahead of it.
This post is provided for general informational purposes only and does not constitute legal, tax, or insurance advice. Contribution limits, notice deadlines, and plan rules can vary and are subject to change; before making benefits decisions, review your actual plan documents and consult a licensed insurance agent, broker, or advisor, and your own legal or tax counsel as appropriate.
Sources
- What are the deadlines for the ACA’s open enrollment period? — healthinsurance.org
- 2026 Open Enrollment Benefit Notices — NIS Benefits
- Medicare Part D Employer Notification Requirements — Savoy Associates
- The 2026 Required Annual Benefit Notices to Employees — Newfront
- IRS Raises FSA, Commuter Contribution Limits for 2026 — HealthEquity
- 2026 FSA, HSA, Retirement Plan Contribution Limits — HRWatchdog
- 2026 Health and Dependent Care FSA Contribution Limits — Saving to Invest