Do I Need to Enroll in Medicare at 65 If I’m Still Working?
- Joel Zimmerle

- Jul 15
- 2 min read
Quick answer: Maybe, but not everyone needs to enroll in every part of Medicare at age 65. The answer usually depends on whether your health insurance comes from current employment, how large the employer is, and what the premium/benefits are compared to Medicare coverage alternatives.
This is one of the most common Medicare questions I get.
Someone is turning 65, still working, and getting health insurance through an employer. They have heard everything from "you have to enroll in Medicare" to "just ignore Medicare until you retire."
The truth is that both answers can be wrong.
Does the size of my employer matter?
Yes, and this is one of the first things I look at.
If your coverage is based on your or your spouse's current employment and the employer has 20 or more employees, the employer plan generally pays first and Medicare pays second. Many people in this situation can delay Medicare Part B without a late enrollment penalty.
If the employer has fewer than 20 employees, Medicare generally pays first after age 65. In that situation, failing to enroll in Medicare on time can create a permanent late enrollment penalty.
There are exceptions, so I never like to make this decision based on the employer's name or someone's best guess but for the most part this is how it works (a quick phone consult allows me to answer this 100% for folks).
Is COBRA the same as active employer coverage?
No.
This is a major Medicare trap. COBRA and retiree health insurance generally do not give you the same ability to delay Medicare Part B that active employer coverage does.
I have seen people assume COBRA protects them so they delay their Medicare Part B coverage, only to learn later that they should have enrolled in Medicare earlier and now have a lifetime late enrollment penalty.
What should I ask my employer before turning 65?
I recommend getting answers to four questions:
Is my insurance based on current active employment?
How many employees does the employer have?
Is my employe coverage considered "creditable coverage" in the eyes of the government?
Is my prescription coverage considered "creditable" for Medicare Part D?
My advice as a Medicare broker
Do not enroll in Medicare just because a friend did. Do not delay Medicare just because a coworker did.
Two people working for different employers can have completely different answers.
I help people across Tennessee look at their current employer coverage, Medicare timing, prescription coverage, and retirement plans before making the decision. There is no fee for my help and a quick phone consult allows me to answer this questions personally for you.
Want help figuring out your Medicare timing? My assistance is of no charge to you.
Joel Zimmerle: Owner/Insurance Broker at Wellness Insurance Partners
Call or text: 615-579-7592
Email: joel@wellnessinsurance.info
Serving Medicare clients throughout Tennessee.

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