COBRA confusion, missed Medigap windows, HSA traps — turning 65 opens a narrow Medicare enrollment window that most people navigate without help. In my years helping Kansas City seniors navigate Medicare, the mistakes I see aren’t random. They’re the same seven mistakes, over and over, costing people thousands of dollars they’ll never get back.
What Is the Biggest Medicare Mistake People Make at 65?
The single most expensive mistake is assuming COBRA coverage lets you delay Medicare enrollment without penalty. It doesn’t. COBRA is not creditable coverage for Medicare purposes. If you leave employer coverage and elect COBRA instead of enrolling in Medicare, you are not in a Special Enrollment Period — you’re in a penalty period.
Can COBRA Replace Medicare When You Turn 65?
No. COBRA is continuation coverage from your former employer’s plan. Medicare does not recognize COBRA as creditable coverage, which means the clock on your Initial Enrollment Period keeps ticking regardless of whether you have COBRA. Miss your window anywhere in the KC metro area and you pay a permanent 10% late enrollment penalty on Part B for every 12 months you delayed.
What Happens If You Miss Your Medicare Enrollment Window?
Your Initial Enrollment Period is 7 months — 3 months before your birthday month, your birthday month, and 3 months after. Miss it without qualifying employer coverage and you face two consequences: a permanent late enrollment penalty on Part B, and you may have to wait until the General Enrollment Period (January 1 - March 31) with coverage not starting until July 1.
How Does Your HSA Change When You Enroll in Medicare?
You must stop contributing to your HSA 6 months before Medicare Part A begins. This catches people off guard because Social Security automatically backdates Part A coverage 6 months when you claim benefits after 65. If you contributed to your HSA during that backdated period, you owe taxes and penalties on those contributions.
Frequently Asked Questions
What is the Medicare Initial Enrollment Period?
Your Initial Enrollment Period is a 7-month window centered on your 65th birthday — 3 months before, your birthday month, and 3 months after. Enrolling in the first 3 months ensures your coverage starts the first day of your birthday month.
Does employer coverage mean I can skip Medicare at 65?
It depends on your employer’s size. If your employer has 20 or more employees, you can delay Medicare without penalty while covered by that plan. If fewer than 20 employees, Medicare becomes primary at 65 and you should enroll immediately.