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Getting Medicare enrollment timing right is one of the most important decisions you'll make. Enroll too late, and you could face permanent penalties that last as long as you have Medicare. Miss your initial enrollment window, and you might have gaps in coverage or pay significantly more for supplemental insurance.
Let me walk you through exactly when to enroll, what it costs, and how to avoid the mistakes that lead to penalties or coverage gaps.
Your Initial Enrollment Period is a 7-month window that begins 3 months before the month you turn 65, includes your birthday month, and extends 3 months after.
Timeline Example (Birthday in June):
Best Practice: Enroll during the 3 months before your 65th birthday. This ensures your coverage starts the first day of your birthday month with no gaps.
Special Rule: If you were born on the 1st of any month, your Medicare coverage actually begins the month before you turn 65.
Whether you need to enroll in Medicare at 65 depends on your employer's size and your coverage type.
You can delay Medicare Part B without penalty if you have creditable coverage through your employer. Your employer coverage remains primary, and Medicare would be secondary if you enrolled.
What to do: Enroll in Part A (it's free), but you can delay Part B. Get documentation from your employer confirming you have creditable coverage.
Medicare becomes your primary insurance at 65. Your employer coverage becomes secondary. You should enroll in both Part A and Part B to avoid gaps in coverage and ensure your employer plan coordinates properly.
What to do: Enroll in Medicare during your Initial Enrollment Period even if you're still working.
Individual health insurance (including ACA marketplace plans) is not considered creditable coverage. You should enroll in Medicare at 65 to avoid late enrollment penalties.
COBRA is not creditable coverage for Medicare purposes. If you're on COBRA when you turn 65, enroll in Medicare during your Initial Enrollment Period.
Every year from October 15 through December 7, you can make changes to your Medicare coverage. Changes take effect January 1.
What you can do during AEP:
Why this matters: Plans change every year. Premiums increase, formularies change, provider networks shift. Reviewing your coverage annually ensures you're still in the best plan for your needs.
From January 1 through March 31, people already enrolled in Medicare Advantage can make one change.
What you can do:
Limitation: You can only make one change during this period.
Certain life events trigger Special Enrollment Periods allowing you to enroll or make changes outside the standard enrollment windows.
Common qualifying events:
Special Enrollment Periods typically last 2-3 months depending on the qualifying event.
If you don't sign up for Part B when you're first eligible and you don't have creditable coverage, you'll pay a permanent penalty.
How it's calculated: 10% of the standard Part B premium for each full 12-month period you could have had Part B but didn't.
2026 Example:
If you don't enroll in Part D when first eligible and go 63 days or more without creditable drug coverage, you'll pay a permanent penalty.
How it's calculated: 1% of the national base premium ($34.70 in 2026) × number of months without coverage.
2026 Example:
High-income earners pay additional premiums for both Part B and Part D based on modified adjusted gross income from two years prior (2024 income affects 2026 premiums).
2026 IRMAA Brackets: Surcharges range from $0 (income ≤$106,000 individual / ≤$212,000 joint) up to $487 monthly Part B surcharge and $85.80 Part D surcharge (income >$500,000 individual / >$750,000 joint).
Life Changes: If your income decreased due to retirement, divorce, or loss of income-producing property, you can appeal your IRMAA determination with documentation.
Part A: $0 premium for most people. $1,736 deductible per benefit period. Daily coinsurance: $434 (days 61-90), $868 (days 91-150).
Part B: $202.90 monthly premium (standard). $283 annual deductible. 20% coinsurance with no maximum.
Part D: Varies by plan ($0-100+/month). Up to $590 deductible. $2,100 out-of-pocket maximum (then $0 for covered drugs).
Medicare Supplement (Medigap): $100-250+/month depending on location, age, and plan choice (Plan G vs. Plan N).
Medicare Advantage: Often $0 additional premium. Copays when using services ($0-50 for doctor visits, $100-400 for hospital stays). Out-of-pocket maximum $3,000-8,000.
Three months before you turn 65, enroll online at ssa.gov/medicare, by phone at 1-800-772-1213, or in person at your local Social Security office.
What you'll need: Social Security number, birth certificate or proof of citizenship, W-2 forms or tax returns (if buying Part A).
Automatic Enrollment: If you're already receiving Social Security benefits at 65, you'll be automatically enrolled in Parts A and B. You'll receive your Medicare card about 3 months before your birthday.
Your Medicare card shows your name, unique Medicare number (not your Social Security number), and coverage start dates for Part A and Part B. Keep it safe but carry it with you—doctors need your Medicare number to bill for services.
Medicare enrollment timing can feel complex, but it comes down to a few key principles: enroll during your Initial Enrollment Period if you don't have creditable coverage, understand how employer coverage affects your timeline, and review your coverage every October during Annual Enrollment Period.
At A&E Insurance Agency, we help you determine exactly when to enroll based on your employment situation, ensure you avoid late enrollment penalties, and coordinate your Medicare enrollment with supplemental coverage decisions. Whether you're three months from turning 65 or already enrolled and considering changes, we'll make sure your enrollment timing and coverage choices work together seamlessly. Schedule a free consultation to review your enrollment timeline and options.
