Missing the Medicare enrollment window at 65 causes permanent premium penalties that last for life.

The Initial Enrollment Period around your 65th birthday cannot be extended for most people. Late enrollment in Part B carries a 10% permanent penalty for each 12-month period of delay. For high-income households, IRMAA surcharges add another layer of planning complexity.

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What changes at the $2M–$30M level

Initial Enrollment Period: 3 months before, the month of, and 3 months after your 65th birthday

Part B late enrollment penalty: 10% per 12-month period of delayed enrollment — permanent

Part D late enrollment penalty: 1% per month of delayed enrollment — permanent

IRMAA surcharges apply to high-income beneficiaries — thresholds are based on income from 2 years prior

Employer coverage rules: if still working, you may be able to delay without penalty — but the rules are specific

Your action plan

Ordered by urgency. Items marked "Immediate" should be addressed within 60–90 days.

⚡ Immediate priority

Confirm your Initial Enrollment Period datesImmediateWithin 90 days

Your window opens 3 months before your 65th birthday and closes 3 months after. Missing it has permanent consequences for most people.

Determine whether your employer coverage allows penalty-free delayImmediateWithin 60 days

Only coverage from an employer where you currently work qualifies for penalty-free delay. COBRA, retiree coverage, and marketplace coverage do not.

⏰ Within 90 days

Model your expected IRMAA surchargesWithin 90 daysWithin 60 days

IRMAA is based on income from 2 years prior. If your income was high in the look-back year, surcharges can add thousands to annual Medicare costs.

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Understand Medigap and Medicare Advantage enrollment rulesWithin 90 daysWithin 90 days

Medigap guaranteed issue rights apply only during your open enrollment window. Missing it means underwriting — and potential denial of coverage.

📋 Within 6 months

Coordinate Medicare with Social Security claiming strategyWithin 6 months

If you delay Social Security past 65, you must enroll in Medicare separately. The coordination between these two decisions matters.

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5-Question Assessment

How prepared are you for medicare at 65?

Answer 5 questions and get a personalized readiness score with specific gaps identified.

1. Do you know your Initial Enrollment Period dates for Medicare?

2. If still working at 65, do you know whether your employer coverage qualifies for penalty-free delay?

3. Have you modeled your expected IRMAA surcharges based on projected income?

+ 2 more questions

Take the medicare at 65 assessment →

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