Quick answer: If you are still working at 65 and covered by your own or your spouse’s employer plan at a company with 20 or more employees, you can usually delay Part B without a penalty, and many people take premium free Part A. If the employer has fewer than 20 employees, Medicare usually pays first and you generally need Parts A and B at 65. COBRA and retiree coverage do not count as current employment coverage.
We help people in Daytona Beach, Ormond Beach, Port Orange, Deltona, New Smyrna Beach and across Volusia County make this call every week. Getting it wrong can mean a lifetime late penalty or a gap in coverage, so confirm the details before you decide.
Two separate decisions: Part A and Part B
Part A (hospital) is premium free for most people with 40 work quarters, so many people take it at 65 even while working. Part B (doctors and outpatient) has a monthly premium, $202.90 in 2026 for most people, so delaying it while you have good employer coverage often makes sense.
HSA warning: once you are enrolled in any part of Medicare, you can no longer contribute to a Health Savings Account. Part A can be backdated up to six months when you sign up after 65, so stop HSA contributions about six months before you enroll.
Questions to ask HR
- How many employees does the company have? (20 or more matters.)
- Is my coverage based on current employment?
- Is the drug coverage creditable for Medicare Part D? Ask for the written notice.
- When does coverage end if I retire or leave?
- Will you complete form CMS-L564 when I enroll in Part B?
Delaying Part B without a penalty
If you delay Part B while covered by a group plan based on current employment, you get an 8 month Special Enrollment Period that starts the month after the job or the coverage ends, whichever comes first. If you miss it, the Part B penalty is 10% for each full 12 months you went without it, for as long as you have Part B.
To enroll later, submit form CMS-40B (Application for Enrollment in Part B) and form CMS-L564 (Request for Employment Information, completed by your employer) to Social Security. Start about two months before your coverage ends so there is no gap.
Common traps
- COBRA is not active employer coverage. Your 8 month window starts when the job ends, not when COBRA ends. Waiting for COBRA to run out can cost you a penalty.
- Retiree coverage also does not let you delay Part B.
- Small employers: with fewer than 20 employees, the plan may pay little or nothing once you are eligible for Medicare.
- Drug coverage: if your employer drug coverage is not creditable, a Part D penalty can apply after 63 days without it.
Covered by a working spouse
The same rules apply when you are on a working spouse’s employer plan. If your spouse retires or loses the job, your 8 month window starts then. Plan both of your timelines together.
When you are ready: two main paths
- Medicare Advantage (Part C): one plan with a local network, copays, and a yearly out of pocket limit, often with drug coverage built in.
- Original Medicare plus a Medicare Supplement and a Part D plan: any doctor in the U.S. that accepts Medicare, with predictable costs. Your best time to buy a Supplement is the six months starting when your Part B begins, when you cannot be turned down for health reasons.
Compare both on our Medicare Advantage vs Supplement in Florida page, or see the full turning 65 timeline.
How we help
USA Benefits Group (HealthBrokerFL) is an independent agency at 913 Big Tree Road in South Daytona. I have been licensed for 14 years, and we are appointed with 80+ insurance companies and licensed in 30+ states. We review your employer plan against Medicare, map out your deadlines, and compare plans for your ZIP code. There is no cost to you because the insurance company pays us.
Bring: your employer plan summary, the creditable coverage notice, your Medicare card if you have one, and your doctor and medication lists.
Call or text 386-401-5644 or email ncurry@healthbrokerfl.com. Office hours are Monday to Friday 9am to 6pm, and Saturday by appointment.
Frequently asked questions
If I am still working at 65, do I have to sign up for Medicare?
Not always. With employer coverage from a company with 20 or more employees, you can usually delay Part B. With fewer than 20 employees, you usually need Parts A and B.
Can I delay Part B without a penalty?
Yes, if you are covered by a group plan based on your or your spouse’s current employment. You then have 8 months after the job or coverage ends to enroll.
Does COBRA let me keep delaying Part B?
No. COBRA does not count as current employment coverage, and your enrollment window starts when the job ends.
Can I take Part A only while I keep working?
Yes, many people do. Stop HSA contributions first, because Part A can be backdated up to six months.
What are forms CMS-40B and CMS-L564?
CMS-40B is the Part B application. CMS-L564 is completed by your employer to prove your group coverage, so you avoid the late penalty.
Does it cost extra to use your agency?
No. There is no cost to you because the insurance company pays us.
We represent all of the Medicare plan organizations available in Volusia County. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.