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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

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.

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).

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.

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.

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.

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.

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).

Choose: Original Medicare OR Medicare Advantage

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

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.

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

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).

Set up your Medicare.gov account

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

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.

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.