You open your renewal notice this fall, and the number staring back is worse than last year’s. You’re not imagining it. Insurers proposed a median increase of about 11 percent for small-group plans entering 2026. Carriers are already asking for another 14 percent for 2027. This cycle also brings new federal rules on your Medicare Part D coverage. It adds a stack of required notices you can’t skip. Maryland is adding a payroll tax to the mix, too. It didn’t exist the last time you ran through open enrollment.

This checklist lays out what to do and when, counting back from your enrollment date, so nothing slips through.

What to Do 90 Days Before Open Enrollment

Ninety days out, the work is about numbers and structure. The paperwork comes later.

Benchmark Your Renewal Numbers

Start by putting your renewal number in context. Nationally, insurers proposed a median increase of about 11 percent for small-group plans entering 2026. Carriers are requesting another 14 percent for 2027. Maryland’s own regulators approved an average increase of 4.9 percent for 2026. Insurers are requesting 13.1 percent for 2027, a figure regulators haven’t approved yet. If your renewal falls well outside these ranges, that’s worth a second look before you sign off on it.

Decide If ICHRA Fits Better Than Group Coverage

Ninety days is enough runway to change plan structure, but not much more than that. An ICHRA, an individual coverage health reimbursement arrangement, lets you set a fixed contribution for each employee. Employees then shop for their own plan on the individual market, rather than all joining a single group policy. For some businesses, that means more predictable costs, more employee choice, and less renewal shock. For others, group coverage is still the right call. A look at the trade-offs between ICHRA and group coverage lays them out side by side. It’s a good place to walk through the decision together with Mark before locking in a direction.

What to Do 60 Days Before Open Enrollment

At 60 days, the focus shifts to compliance, before any of it goes to print.

Confirm Your Medicare Part D Creditable Coverage Status

The federal standard for Medicare Part D creditable coverage got harder to meet this year. In plain terms, your plan’s drug benefit now has to measure up more closely to Medicare’s own standard. For 2026, CMS’s finalized rule lets you test your plan against either the old 60 percent standard or a tougher 72 percent one. Starting in 2027, only the higher bar applies, rising again to 73 percent alongside a new $2,100 out-of-pocket cap. A plan that passed easily under the old test can fail the new one with no changes on your end. Federal rules require you to notify employees whether your plan is creditable, one way or the other, before October 15. Getting that notice wrong, or skipping it, can leave a Medicare-eligible employee facing a permanent late-enrollment penalty down the road.

If you’re an applicable large employer under the ACA, generally 50 or more full-time employees, one more number belongs on this list. The IRS set the 2026 affordability threshold at 9.96 percent of an employee’s pay, the highest it’s been. That figure caps how much you can charge an employee for your lowest-cost, self-only plan before the coverage counts as unaffordable under federal law.

Check the Rest of Your Required Notice Stack

Part D isn’t the only notice due this cycle. Your enrollment packet also needs:

• A current Summary of Benefits and Coverage (SBC) document
• A COBRA notice explaining how departing employees can keep coverage temporarily
• The CHIP notice about state children’s health coverage
• A HIPAA notice covering special enrollment rights for events like marriage or a new baby

Missing any of these carries its own penalty exposure under federal law. None of them change dramatically year to year. You do need to keep every one current and send it out on time. Sixty days out is when to pull last year’s packet and check the templates against this year’s plan details. Then queue every notice to go out with the rest of your enrollment materials.

What to Do 30 Days Before Open Enrollment

Add Maryland’s FAMLI Notice If You Have Employees Here

If you have employees working in Maryland, this year’s enrollment materials need one more document. It’s the state’s required notice about Maryland’s paid family and medical leave program, called FAMLI. The FAMLI payroll tax runs at 0.9 percent of wages, split evenly between employer and employee. Businesses with fewer than 15 employees don’t owe an employer share at all. The tax itself starts January 1, 2027, but the notice requirement lands sooner. You have to tell employees, in writing, about the coming payroll deduction before December 2026, one pay period ahead of the first withholding. A closer look at Maryland’s FAMLI notice requirements explains what has to be in that notice. It also covers when the notice needs to go out.

What to Do During the Enrollment Window

Once the window opens, the job shifts from paperwork to people.

Give Employees Enough Time to Decide

Employees facing an insurance decision need real time to think it through, not a rushed reply by Friday. Give your team at least two full weeks inside the enrollment window. Write plan summaries and cost breakdowns in plain English, not the carrier’s own wording. A parent weighing coverage for a new baby, or an employee managing a chronic condition, is making a real decision. It affects their family’s health and budget for the whole next year. The clearer the information, the more confident that decision feels.

Offer a Short List of Voluntary Benefits

A short, well-chosen list works better than an overwhelming one. Offer Life Insurance, Short-Term Disability, and maybe a legal or pet-insurance option. Employees can then add protection where it matters, on their own dime, without facing a crowded menu of options. Ten choices, presented well, beat forty choices in a spreadsheet.

What to Do After Open Enrollment Closes

Once the window closes, the job isn’t over yet. Plan documents, payroll systems, and any employee-facing summaries need to reflect whatever changed this cycle. That might be a new ICHRA structure, an updated Part D notice, or a plan that ended mid-cycle. This is also the moment to write down what went sideways this year. Maybe it was a confusing form, a missed deadline, or a carrier that took too long to respond. Next year’s renewal should start from a shorter list of problems instead of the same one.

Closing — You Don’t Have to Get This Right Alone

This is a lot to track for a business that also has to keep running while it happens. That’s exactly why Mark built this practice around the 2 to 50 employee range. These are businesses without a dedicated benefits team to sit through Part D thresholds and tax notices for a living. Maybe this checklist raised more questions than it answered. If so, reach out to Mark whenever you’re ready, and he’ll confirm the details before you sign off. He’s been doing this since 2001. The goal is the same every year, the right coverage for your team, not just whatever renewed automatically.