Common Medicare Mistakes People Make When First Enrolling

Most Medicare regrets trace back to a handful of first-enrollment mistakes. Almost all of them are preventable.

Mistake 1: Missing the Initial Enrollment Period

Your Initial Enrollment Period is 7 months long. Miss it and you may face a lifelong Part B late enrollment penalty and a lifelong Part D penalty (if you also go without creditable drug coverage).

Mistake 2: Assuming Employer Coverage Always Replaces Part B

• Employer with 20+ employees → employer coverage is usually primary.
• Employer with under 20 employees → Medicare is usually primary.

Always verify your coverage's primary/secondary status in writing.

Mistake 3: Relying on COBRA Alone After 65

COBRA does not count as active employer coverage for Part B SEP purposes. Many people assume COBRA protects them, miss the deadline, and end up with a permanent penalty. See Medicare SEP After Losing Employer Coverage.

Mistake 4: Choosing a Plan Based on TV or a Mailer

Medicare ads are marketing, not guidance. Real choice should be based on your doctors, your medications, your county's plan availability, and your budget.

Mistake 5: Skipping Part D Because You Don't Take Medications

Part D at Medicare eligibility protects you from a lifelong Part D late enrollment penalty. Many low-premium Part D plans exist. See How Medicare Part D Works in Kentucky.

Mistake 6: Choosing Medicare Advantage Without Checking the Network

A $0-premium plan is not helpful if your doctor is out-of-network. Read Medicare Advantage: What to Compare First.

Mistake 7: Choosing Medigap Without Shopping Carriers

Medigap plan letters are standardized, but premiums vary significantly between carriers for the same plan letter.

Mistake 8: Assuming You Can Easily Switch From Advantage to Medigap Later

In Kentucky, switching from MA to Medigap after the initial windows can require medical underwriting. Read Medigap vs Medicare Advantage for Different Situations.

Mistake 9: Ignoring Dental, Vision, and Hearing Gaps

Original Medicare doesn't cover routine dental, vision, or hearing. Without a plan for those gaps — either MA with extras or standalone dental and vision — costs can hit unexpectedly.

Mistake 10: Treating Medicare Enrollment as a One-Time Event

Plans change every year. Build an annual review habit — see How to Review Your Medicare Plan Every Year.

Quick Prevention Checklist

• Enroll on time (IEP, SEP, or AEP as applicable).
• Confirm primary/secondary status of any employer coverage.
• Do not rely on COBRA after 65.
• Check networks and formularies for every plan you consider.
• Shop Medigap carriers on price.
• Review annually.

We are a licensed independent agency based in Somerset, Kentucky, serving clients throughout Kentucky. We walk new-to-Medicare clients through this list one item at a time.