MEDICARE'S MOST COMMON ENROLLMENT MISTAKES
- Michael Braden
- Aug 23
- 5 min read
Updated: Aug 25
Michael T. Braden, August 23, 2025 MEDICARE ENROLLMENT

After reading this article, you will know more about Medicare, Medicare Enrollment Periods, and how to avoid common mistakes.
Medicare is pretty simple once you get used to it, but it can certainly be confusing when you first start researching it, and especially when you first enroll in Medicare. We have seen the best-intentioned people make mistakes that could have been easily avoided if they had only asked for help. Therefore, we are dedicating this article to everyone who wishes they had a mulligan when they first enrolled in Medicare.
DELAYING YOUR MEDICARE START DATE BASED ON YOUR ENROLLMENT DATE
Medicare has several separate Enrollment Periods each year (AEP, IEP, OEP, SEP), which can make things pretty confusing for anyone. But your Initial Enrollment Period (IEP) is by far the most important one of them all.
There can be consequences and penalties if a new Medicare Beneficiary does not enroll in Medicare within their IEP, provided they have no other "Creditable Medical Coverage", such as a Group Employer Health Plan from a company with more than 20 Employees, or FEHB Members.
Everyone has the same Initial Enrollment Period for Medicare. It is the Seven-Month Period that starts three months before your birth month and ends three months after your birth month.
Many people who have Group Health Insurance from their employer and have decided to work past Age 65 can choose to delay their IEP until they retire and their Group Health Insurance ends. For these people, their IEP will begin once their Group Health Insurance ends.
COBRA IS NOT CONSIDERED CREDITABLE COVERAGE BY MEDICARE
Many people dislike the cost of having COBRA coverage as a short-term solution for Maintaining Health Insurance from the time they retire from their employer until
Medicare coverage begins. The price is outrageous, but perhaps the worst thing is
that it gives people a false sense of security. This is because, although it is considered health coverage, no COBRA plan is approved by Medicare (CMS) to be health insurance that is at least equal to Medicare.
Because COBRA plans are not standardized, they can vary significantly from person to person and company to company. You must remember to enroll in a qualified Medicare Plan during your Initial Enrollment Period (IEP). If you do not enroll into a qualifying Medicare Plan, Original Medicare, or a Medicare Advantage Plan (Medicare Part C), you could be subject to paying a Medicare Penalty for life.
3. NOT UNDERSTANDING WHAT IT MEANS IF YOU WORK FOR A SMALL EMPLOYER
Did you know that Medicare categorizes Group Health Insurance (Employer Group Health Benefits) into two categories, based on the number of employees it covers? Medicare indeed defines "small" employers as those with fewer than 20 employees, and they refer to employers with more than 20 employees as "large" employers.
Why does the size of the company matter? Well, Medicare does not classify Small Employer Group Health Coverage as being creditable, and, as such, you must enroll in Medicare as soon as you turn 65. Small Employers are not allowed to offer health insurance to anyone once they turn 65. This means that you need to be enrolled in Medicare before you are three months past your birth month! If you do not enroll in Medicare during your Annual Enrollment Period, Medicare will impose a Part B and possibly a Part D Late Enrollment Penalty that never goes away..
Because COBRA plans are not standardized, they can vary significantly from person to person and company to company. It is essential to remember that you must enroll in a qualified Medicare Plan during your Initial Enrollment Period (IEP). If you do not enroll into a qualifying Medicare Plan, Original Medicare, or a Medicare Advantage Plan (Medicare Part C), you could be subject to paying a Medicare Penalty for life.
BILLING ISSUES AND YOUR PART B DEDUCTIBLE
Perhaps the biggest problem most people have in their first year of enrolling in Medicare is billing errors. This is because your Doctor will bill Medicare, or your Medicare Advantage Plan, directly after you have paid any co-insurance or copay amounts when you receive services. Unfortunately, for those with a Medigap or Medicare Supplement plan, doctors' offices often send a bill to your insurance in addition to Medicare. This can create an unnecessary mess.
Many people who have chosen Original Medicare forget that they must meet the Medicare Part B deductible before Medicare will pay for any services. Depending on where you live, the deductible can be paid at the doctor's office, or you may receive a bill/invoice from Medicare.
It is essential to note that the doctor/provider bills Medicare (if you have Original or Traditional Medicare), and Medicare will then send any remaining balance to your supplemental carrier for payment. It is not permitted for a provider or doctor to text, email, call, or harass a Medicare beneficiary for payment. If they have questions, they should contact Medicare (CMS) directly.
Here at Braden Medicare Insurance, we have developed a "Patient Information Cover Sheet" that we give to each of our clients. We have found that it has dramatically reduced billing errors and is a valuable tool. If you are interested in this or would like to learn more about how it works, please don't hesitate to reach out to us.
5. THINGS TO REMEMBER DURING THE MEDICARE ANNUAL ENROLLMENT PERIOD (AEP)
The Medicare Annual Enrollment Period takes place every Fall, from October 15th through December 7th.

During the AEP, you can pick a new Medicare Advantage or a new Medicare Part D Prescription Drug plan for the new year beginning on January 1st. You can switch from Original Medicare to a Medicare Advantage plan, and your changes will take effect on January 1st. You can leave your Medicare Advantage plan and re-enroll in Original Medicare, effective January 1st.
If you have a Stand-Alone Medicare Part D PDP plan and are satisfied with it, and the plan is available for the next year, you do not need to take any action; your plan will automatically renew.
Lastly, if you have chosen Original/Traditional Medicare with a Medicare Supplement/Medigap plan, you do not need to do anything during the Medicare AEP (Annual Enrollment Period). This is because once you purchase a Medigap policy, it is considered to be permanent. You can always apply for a new Medicare Supplement/Medigap plan with the same or a different carrier, any day of the year.
WRAPPING THINGS UP
Medicare has numerous rules, regulations, and protocols. However, once you are aware of them, things should proceed smoothly, and most people are generally satisfied with Medicare. If you have any questions, please don't hesitate to contact your broker. If you do not have your own Medicare Broker, feel free to call us anytime; we are always happy to answer questions.

_AZ_Initial.png)






