Clients Working Past 65: Medicare Rules Every Agent Should Know
In short: Clients covered by a group health plan through current employment at a company with 20 or more employees can usually delay Part B without a penalty. Many still take premium-free Part A. If the employer has fewer than 20 employees, Medicare usually pays first, so clients should enroll in Parts A and B when first eligible. When work or coverage ends, clients get 8 months to sign up for Part B without a penalty.
More of your prospects are working into their late 60s and beyond. Many assume they don’t need to think about Medicare until they retire. Others sign up for everything at 65 when they didn’t need to.
Agents who understand these rules prevent costly mistakes. They also earn the trust of clients who will need them when they do retire.
Why Does Employer Size Matter?
Employer size decides who pays first. This one fact shapes the whole conversation.
| Employer size | Who pays first | What clients usually do |
|---|---|---|
| 20 or more employees | The employer plan | Keep the group plan, often take premium-free Part A and delay Part B |
| Fewer than 20 employees | Medicare | Enroll in Parts A and B when first eligible, about 3 months before the 65th birthday month |
The same rules apply when a client is covered through a spouse’s current employment. Always confirm with the employer’s HR or benefits team in writing.
What Questions Should I Ask a Client Who Is Still Working?
- Is your coverage based on current, active employment?
- How many employees does your employer have?
- Does your plan pay first or second to Medicare?
- Do you contribute to a Health Savings Account (HSA)?
- Is your drug coverage creditable? (Employers send an annual notice.)
- When do you plan to retire, and will you have retiree or COBRA coverage?
These answers tell you whether to enroll now, delay Part B or compare the employer plan side by side with Medicare.
How Does the Part B Special Enrollment Period Work?
Clients who delayed Part B because of current employment coverage get a Special Enrollment Period. They can sign up while still on the group plan or during the 8 months after employment or coverage ends, whichever comes first.
Coach clients not to wait until the end of that window. Enrolling a month or two before coverage ends prevents a gap.
They’ll usually need two forms:
- CMS-40B, the Application for Enrollment in Part B.
- CMS-L564, the Request for Employment Information, completed by the employer.
Their 6-month Medigap Open Enrollment Period also starts when Part B begins. That’s the best time to buy a Medicare Supplement without underwriting. See our Medicare enrollment periods cheat sheet for every window.
What Traps Catch Clients Most Often?
- COBRA and retiree coverage. Neither counts as coverage based on current employment. Delaying Part B while on COBRA can lead to a late penalty and a coverage gap.
- HSA contributions. Once a client enrolls in any part of Medicare, including Part A, they can’t contribute to an HSA. Part A can be backdated up to 6 months, so they should stop contributions ahead of time.
- Small employers. Clients at companies with fewer than 20 employees who skip Part B may find their group plan won’t pay claims Medicare should have paid first.
- Non-creditable drug coverage. Without creditable coverage, clients may face a Part D late penalty later.
How Do I Turn These Clients Into Long-Term Relationships?
Clients who are still working may not enroll with you today. That’s fine. Stay in touch.
- Add their expected retirement date to your CRM.
- Check in once a year and when their employer plan renews.
- Reach out about 3 months before their coverage ends.
- Review life insurance and final expense needs as they plan retirement.
When they’re ready, you’ll be the agent they trust. Our turning-65 guide covers the rest of the enrollment process.
How Does Lourie Agent Partners Help With Complex Enrollments?
Working-past-65 cases raise detailed questions. You don’t have to answer them alone.
- Phone support every business day, including help while you’re in an appointment.
- Training on Special Enrollment Periods and coordinating Medicare with other coverage, through workshops, webinars and bi-weekly partner calls.
- Free myLourie CRM to track retirement dates and follow-ups.
- Direct carrier appointments, commissions paid directly to you and full vesting from day one.
Learn more about our service and support.
Frequently Asked Questions
Usually yes, if the employer has 20 or more employees and the coverage is based on current employment. Confirm with the employer’s benefits team first.
No. COBRA isn’t coverage based on current employment, so delaying Part B can lead to a late enrollment penalty.
No. Contributions must stop once any part of Medicare begins. Because Part A can be backdated up to 6 months, clients should stop contributing about 6 months before they apply.
Usually form CMS-40B and form CMS-L564, which the employer completes.
If you partner with Lourie Agent Partners, call our support team. We help agents with complex cases every business day.
Be the Agent Clients Call When They Retire
Getting the timing right protects your clients from penalties and gaps. Let our team back you up on every complex case. Get contracted with Lourie Agent Partners or call (803) 256-2067.