10/19/2026
Open enrollment season is here but not everyone is working toward the same deadline.
Your employees may be hearing about Medicare enrollment and your company’s benefits enrollment at the same time. It’s easy to get confused, put it off, or choose the same plan without taking a closer look.
Picture a 40-person company that sends one email saying “Open enrollment is November 1–15. Pick your plan.” And that’s the entire communication plan.
Then January comes. An employee learns their prescription isn’t covered. Another finds out their doctor is out of network. Someone’s payroll deduction isn’t what they expected.
That doesn’t necessarily mean anyone was careless. It may mean the communication explained when to enroll—but not what to review or where to get help.
Here’s a starting point you can share with your team:
📅 Medicare Annual Enrollment: October 15–December 7, 2026
For people already on Medicare, this is a time to review Medicare Advantage and Part D prescription drug plans, including doctors, prescriptions, and costs. Changes take effect January 1, 2027.
📅 Your company’s open enrollment: Your dates, your deadline
There’s no single federal open enrollment date for employer plans. Give employees your specific enrollment window, the deadline, where to compare plans, and instructions for making their elections.
Then make these reminders part of the conversation:
- Keeping the same plan? Review it anyway. Provider networks, covered prescriptions, deductibles, and other costs can change.
- Look beyond the premium. Compare what comes out of each paycheck with what you may pay when you actually need care.
- Know where to get help. Use Medicare.gov for Medicare questions and your benefits contact or carrier for your company plan.
And one step for the employer or the HR team:
Before the first payroll of the new plan year, check that employee elections, carrier records, and payroll deductions match. Catching a discrepancy early is much easier than untangling it months later.
You don’t have to turn every employee into a benefits expert. But you do need to make the deadline clear the next step obvious, and help easy to find.
