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Top Mistakes When Enrolling in Medicare

A handful of enrollment mistakes can lead to lifelong penalties — here's what to double-check.

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Enrollment Timing Mistakes

Automatic enrollment into Original Medicare only happens if you're already receiving Social Security benefits. If you're not, you need to actively sign up during your Initial Enrollment Period — the seven-month window around your 65th birthday.

If you're still working with employer coverage when you turn 65, whether you can delay Medicare penalty-free depends on your employer's size. Generally, employers with 20 or more employees let you delay Medicare without penalty, while smaller employers do not. COBRA coverage does not count as a qualifying reason to delay Medicare.

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Penalty and Coverage Mistakes

Missing your enrollment window can trigger permanent late enrollment penalties. The Part B penalty generally adds a percentage to your premium for each 12-month period you were eligible but not enrolled, for as long as you have Part B. The Part D penalty applies if you go 63 or more consecutive days without creditable drug coverage after becoming eligible.

It's also worth understanding that Original Medicare alone has no annual out-of-pocket maximum, while Medicare Advantage plans do — a distinction that matters if you're weighing the two paths.

Frequently Asked Questions

It depends on your employer's size. If your employer has 20 or more employees, you can generally delay Medicare penalty-free. Smaller employers usually require you to enroll in Medicare at 65.