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5 Costly Medicare Mistakes to Avoid at 65

A few enrollment missteps at 65 can lead to penalties that follow you for years.

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Timing and Penalty Mistakes

Assuming you're automatically enrolled: automatic enrollment only happens if you're already receiving Social Security benefits. Otherwise, you need to actively sign up during your seven-month Initial Enrollment Period.

Assuming employer coverage always lets you delay Medicare penalty-free: this generally only applies if your employer has 20 or more employees. Smaller employers usually require enrolling in Medicare at 65 regardless. And COBRA doesn't count as a qualifying reason to delay Medicare either.

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Coverage and Network Mistakes

Missing your enrollment window entirely: the Part B penalty generally adds a percentage to your premium for each 12-month period you were eligible but didn't enroll, and it typically lasts as long as you have Part B. The Part D penalty applies after 63 or more consecutive days without creditable drug coverage.

Not understanding the cost-sharing difference between Original Medicare and Medicare Advantage: Original Medicare has no annual out-of-pocket maximum on its own, while Medicare Advantage plans do — and choosing a plan without checking network access to your current doctors is one of the most common regrets people report after enrolling.

Frequently Asked Questions

Assuming enrollment is automatic. Unless you're already receiving Social Security, you need to actively sign up during your Initial Enrollment Period.