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Medicare Enrollment Checklist

A step-by-step guide to ensure smooth enrollment and avoid costly penalties

📅 3–6 Months Before Your 65th Birthday

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Understand your options

Learn the difference between Original Medicare (Parts A & B) and Medicare Advantage (Part C). Read our Medicare 101 guide for a comprehensive overview.

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Check your Social Security status

If you're already receiving Social Security benefits, you'll be automatically enrolled in Parts A and B. If not, you'll need to actively sign up during your Initial Enrollment Period (IEP).

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Review employer/union coverage

If you have group health insurance through an employer with 20+ employees, you may be able to delay Part B enrollment without penalty. Request a creditable coverage letter from your employer's HR department to confirm this.

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List your medications

Create a complete list of all prescription drugs including name, dosage, frequency, and pharmacy. You'll need this to compare Part D and MAPD formularies.

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Identify your doctors and specialists

If you're considering Medicare Advantage, you'll need to verify your current providers are in-network. Make a list of all doctors, specialists, and hospitals you use.

📝 During Your Initial Enrollment Period

Your IEP is a 7-month window: 3 months before your 65th birthday month, the birthday month itself, and 3 months after.

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Enroll in Part A (Hospital Insurance)

Sign up at ssa.gov or your local Social Security office. Part A is premium-free for most people and there's no reason to delay it.

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Decide on Part B enrollment

If you don't have creditable employer coverage, enroll in Part B during your IEP to avoid the permanent late enrollment penalty (10% per year of delay).

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Choose: Original Medicare OR Medicare Advantage

This is the biggest decision. See our MA vs. Medigap comparison to understand the trade-offs.

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If Original Medicare: Add a Medigap plan

Your first 6 months on Part B are the Medigap Open Enrollment Period — the only time insurers must accept you regardless of health status. Don't miss this window.

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Add Part D drug coverage

Either as a standalone PDP (with Original Medicare) or as part of an MAPD plan. Delaying enrollment without creditable coverage triggers a permanent penalty of 1% per month.

⚠️ Critical: The penalties for late Part B and Part D enrollment are permanent — they last for life. Missing your IEP can cost thousands of dollars over time.

✅ After Enrollment

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Verify your Medicare card arrived

Your red, white, and blue Medicare card should arrive within a few weeks of enrollment. It lists your Medicare Beneficiary Identifier (MBI).

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Set up your Medicare.gov account

Create an account at medicare.gov to view your coverage, claims, and preventive services schedule.

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Schedule your "Welcome to Medicare" visit

This free preventive visit is available within the first 12 months of Part B enrollment. It includes a health risk assessment, depression screening, and advance care planning discussion.

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Review your plan annually during AEP

Each year during AEP (Oct 15 – Dec 7), compare your current plan against other options. Plans change their formularies, premiums, and networks every year.

💡 Pro tip: Bookmark the MultiHealthOptions dashboard for quick access to all major carrier portals, eligibility tools, and plan comparison resources.