MEDICARE ELIGIBILITY PLANNING
Turning 65?
Let's Plan This Right.
Medicare enrollment has strict deadlines with permanent consequences for missing them. Start your planning conversation 3–6 months before your 65th birthday.
YOUR MEDICARE TRANSITION
Medicare Is One of the Most
Important Financial Decisions You'll Make
Turning 65 is exciting but the Medicare enrollment process is surprisingly complex. There are multiple parts, enrollment windows, coordination rules, and decisions that interact with each other in ways that aren't always obvious. Making the wrong choice or missing a deadline can result in coverage gaps, permanent premium penalties, or being locked into a plan that doesn't fit your needs.
Our Turning 65 planning service is designed to walk you through every decision in the right order, at the right time, so you start your Medicare coverage with confidence and without costly mistakes.
When Should You Start Planning?
We recommend reaching out 3 to 6 months before your 65th birthday. This gives us enough time to map your specific enrollment dates, coordinate with any existing employer or retiree coverage, and complete your enrollment applications without rushing.
Your Initial Enrollment Period (IEP)
Your Initial Enrollment Period is a 7-month window — it begins 3 months before the month you turn 65, includes your birthday month, and extends 3 months after. Enrolling in the first 3 months of your IEP ensures your coverage starts on time. Waiting until after your birthday month can delay coverage by 1–3 months.
Step 1 — Understand Medicare Parts A and B
Part A (Hospital Insurance) covers inpatient hospital stays, skilled nursing facility care, hospice, and some home health services. Most people pay $0 premium for Part A if they or their spouse worked and paid Medicare taxes for at least 10 years.
Part B (Medical Insurance) covers outpatient services, doctor visits, preventive care, lab tests, durable medical equipment, and some home health services. The standard Part B premium in 2026 is $202.90/month, deducted from your Social Security benefit if you're collecting it.
Step 2 — The Critical Question: Are You Still Working?
Whether you're still working and whether your employer has 20 or more employees dramatically affects when you need to enroll in Medicare, and what happens if you delay.
⟶ Large employer (20+ employees): Your employer coverage is primary. You can delay Part B without penalty while you have employer coverage. Medicare would be secondary if you also enroll.
⟶ Small employer (under 20 employees): Medicare becomes primary at 65 regardless. Failing to enroll in Part B can leave you with significant gaps in coverage.
⟶ Self-employed or no employer coverage: Enroll in Medicare during your Initial Enrollment Period to avoid late penalties.
⟶ Retiring at 65: You'll typically have a Special Enrollment Period to sign up for Medicare when your employer coverage ends; coordinate timing carefully to avoid gaps.
Step 3 — Choose Your Coverage Path
Once you have Parts A and B, you choose how to receive the rest of your Medicare coverage. This is the decision most people find most confusing and it's where we add the most value.
Path 1: Medicare Advantage (Part C)
An all-in-one plan from a private insurer that replaces Original Medicare as your primary coverage. Often includes prescription drugs, dental, vision, and hearing. Network-based. Often $0 premium. Best for people who want simplicity and extra benefits at low cost and are comfortable with network restrictions.
Path 2: Original Medicare + Medigap + Part D
Keep Original Medicare as your primary coverage, add a Medigap plan to cover the gaps, and add a standalone Part D plan for prescriptions. No networks, see any Medicare provider nationwide. Predictable costs. Higher monthly premium than most MA plans. Best for people who want maximum flexibility and predictable out-of-pocket costs.
The Decision That's Hard to Undo
Choosing Medigap at 65 during your open enrollment period is the only time you're guaranteed acceptance regardless of health conditions. If you start with Medicare Advantage and later want to switch to Medigap, you may face medical underwriting and could be denied or charged significantly more. This is one reason why thinking through your long-term needs at 65 matters so much and why we take the time to have this conversation thoroughly.
Step 4 — Add Prescription Drug Coverage
If you choose Medigap, you need a standalone Part D drug plan. We analyze your complete medication list against every available plan in Ohio to find your lowest total annual drug cost, not just the lowest premium.
If you choose Medicare Advantage, most plans include drug coverage, but we still verify that your specific medications are covered at acceptable cost tiers before recommending any plan.
Step 5 — How Medicare Fits Your Retirement Picture
This is where our background in financial services gives you a conversation most Medicare agencies can't offer. Medicare decisions don't exist in isolation they connect directly to your retirement income plan:
⟶ Social Security timing: If you delay Social Security past 65, you'll need to enroll in Medicare Part B separately and set up a payment method for your premium
⟶ IRMAA planning: Higher income means higher Medicare premiums — understanding your income thresholds helps with retirement income planning
⟶ Healthcare cost projections: We help you understand what Medicare will actually cost you annually so you can plan your retirement budget accurately
⟶ HSA accounts: You must stop contributing to an HSA once you enroll in any part of Medicare — timing your enrollment affects your HSA strategy
COMMON QUESTIONS
Part D Prescription Plans FAQ
Does Medicare start automatically at 65?
Part A may start automatically if you're already collecting Social Security. Part B is not automatic you must actively enroll. If you're not collecting Social Security at 65, you'll need to contact Social Security to enroll in both Parts A and B during your Initial Enrollment Period.
What if I miss my Initial Enrollment Period?
Missing your IEP without qualifying employer coverage can result in permanent late enrollment penalties for Part B (10% per 12-month period you delay) and Part D (1% per month without creditable coverage). These penalties last for life. This is exactly why early planning matters.
Can I have Medicare and employer insurance at the same time?
Yes, but understanding which plan is primary is critical. The rules depend on your employer's size and your specific situation. Coordinating dual coverage incorrectly can result in claim denials. We work through this coordination for every client with dual coverage.
What does Medicare cost at 65?
Part A is typically $0/month. Part B is $202.90/month in 2026 (higher for higher incomes). Add a Medigap plan ($120–$230/month) and Part D ($5–$80/month) for a full coverage picture. Or choose a $0-premium Medicare Advantage plan. Total monthly costs range from $202.90 to $400+ depending on the path you choose..
Do I need Medicare if I have VA benefits?
VA benefits and Medicare are separate programs. VA coverage only works at VA facilities for VA-approved care. Medicare gives you access to any Medicare provider nationwide. Many veterans choose to have both to maximize their options, particularly for emergency care outside VA facilities.
When should I stop contributing to my HSA?
You must stop HSA contributions once you enroll in any part of Medicare including Part A. If you delay Medicare enrollment while working, you can continue HSA contributions. This is an important consideration for people who want to maximize their HSA before transitioning to Medicare.