New to Medicare Turning 65
New to Medicare Turning 65 , ready for medicare enrollment should feel like a milestone worth celebrating. But for most people, it feels like walking into a fog.
You know you need Medicare. You’ve heard the horror stories about penalties and missed deadlines. But you’re not sure when to enroll, what to enroll in, or whether you even need it yet.
And everyone you talk to has a different answer.
Your neighbor says you don’t need it if you’re still working. Your cousin says you should sign up three months early. Your friend says Medicare doesn’t cover anything. And your insurance agent keeps pushing a plan you’re not sure you understand.
Here’s the truth: Medicare at 65 isn’t automatic. It’s not one-size-fits-all. And the choices you make in the next few months will affect your coverage and your costs for years to come.
I treat every client like I would my own parents. And if my parents were new to medicare turning 65 and enrolling, here’s exactly what I’d walk them through — step by step, with no confusion and no pressure.
Who Must Enroll in Medicare at 65
Not everyone needs to enroll in Medicare when turning 65. But most people do.
Here’s who must sign up:
You’re retired or not working. If you don’t have employer coverage, you need Medicare. There’s no exception. Enroll during your Initial Enrollment Period or you’ll face penalties.
You work for a small employer (19 or fewer employees). Even if you’re still working, Medicare becomes your primary insurance at 65. Your employer plan becomes secondary. If you don’t enroll, your employer plan may deny claims, leaving you stuck with the bills.
You’re on an ACA marketplace plan. Once you turn 65, you’re no longer eligible for ACA subsidies or tax credits. You must transition to Medicare. If you stay on your ACA plan, you’ll pay full price — and it’s not cheap.
You’re on COBRA. COBRA doesn’t replace Medicare. Once you turn 65, Medicare becomes primary. COBRA won’t protect you from penalties or coverage gaps. Enroll in Medicare, then keep COBRA only if you need it for specific providers or drugs. Learn more about how COBRA and Medicare work together.
You’re a retired service member with Tricare. If you have Tricare, you must enroll in Medicare Part A and Part B at 65. Without Part B, Tricare For Life won’t work. Medicare pays first, and Tricare covers what’s left. Learn more about Medicare and VA healthcare.
You’re already collecting Social Security. If you’re receiving Social Security benefits when you turn 65, you’ll be automatically enrolled in Medicare Parts A and B. Your Medicare card will arrive in the mail about three months before your 65th birthday. You don’t need to do anything unless you want to opt out of Part B (which you shouldn’t do unless you have creditable employer coverage).
Who Can Delay Medicare at 65
There’s one group that can delay Medicare without penalties: people with creditable employer coverage from a company with 20 or more employees.
If that’s you, you can stay on your employer plan and delay Medicare Part B and Part D without penalties. But you need to get that confirmed in writing from your HR department.
Once your employment or coverage ends, you have an eight-month Special Enrollment Period to enroll in Medicare. Miss that window, and you’ll face penalties for the rest of your life.
Learn more about whether you need Medicare if you’re still working and how Medicare and employer insurance compare.
Understanding Primary vs. Secondary Payer Rules
Here’s something that trips people up: if you have Medicare and another type of coverage, one pays first (primary) and the other pays second (secondary).
Getting this wrong can lead to denied claims, surprise bills, and a lot of frustration.
When Medicare is primary:
- You’re retired and no longer have employer coverage
- You work for a small employer with 19 or fewer employees
- You’re on COBRA
- You’re on an ACA plan
- You have Tricare as a retiree
When Medicare is secondary:
- You work for a large employer (20+ employees) and have active group coverage
- Your spouse works for a large employer and you’re covered under their plan
If Medicare is primary and you don’t enroll, your other insurance will deny claims. You’ll be stuck paying out of pocket.
Always show both insurance cards at the doctor’s office. Confirm with your HR department or insurer who pays first. And enroll in Medicare on time to avoid gaps.
Key Deadlines: Your Initial Enrollment Period Timeline
Your Initial Enrollment Period is a seven-month window around your 65th birthday. It’s the most important deadline for turning 65 Medicare enrollment, and missing it can cost you thousands.
Here’s how it works:
Three months before your birthday month: This is the best time to enroll. If you sign up during these three months, your Medicare coverage will start on the first day of your birthday month. No gaps. No delays.
Your birthday month: You can still enroll, but your coverage will start the month after your birthday. That means a one-month gap if you’re not careful.
Three months after your birthday month: You can still enroll without penalties, but your coverage will be delayed even further. Enroll in the first month after your birthday, and coverage starts two months later. Enroll in the second month after, and it starts three months later. And so on.
What if I miss my Initial Enrollment Period?
If you miss the entire seven-month window and you don’t have creditable employer coverage, you’re stuck waiting until the General Enrollment Period (January 1 – March 31). Your coverage won’t start until July 1.
And you’ll face penalties:
- Part B penalty: 10% added to your premium for every 12 months you were eligible but didn’t enroll. This penalty lasts for life.
- Part D penalty: 1% of the national base premium for every month you went without creditable drug coverage. This penalty also lasts for life.
Don’t let that happen. Enroll early. Learn more about Medicare late enrollment penalties.
Special Rules for ACA, Tricare, and COBRA Members
If you’re on an ACA plan, Tricare, or COBRA, you need to pay close attention. The rules change at 65, and if you don’t transition to Medicare properly, you’ll face gaps, penalties, and higher costs.
ACA Marketplace Plans
Once you turn 65, you’re no longer eligible for ACA subsidies or tax credits. Your marketplace plan becomes expensive — fast.
You must enroll in Medicare during your Initial Enrollment Period. If you don’t, you’ll lose your subsidies and you’ll pay full price for your ACA plan. And that’s usually a lot more than Medicare would cost.
Enroll in Medicare on time, then drop your ACA plan. No exceptions.
Tricare
If you have Tricare as a retiree, you must enroll in Medicare Part A and Part B at 65. Without Part B, Tricare For Life won’t work.
Medicare becomes your primary insurance. Tricare becomes secondary, covering what Medicare doesn’t pay.
If you skip Medicare, you’ll lose your Tricare benefits and you’ll be stuck paying out of pocket. Don’t make that mistake.
COBRA
COBRA is continuation coverage from a former employer. It’s not creditable for Medicare purposes, which means it doesn’t let you delay Part B or Part D without penalties.
Once you turn 65, Medicare becomes primary. COBRA becomes secondary. If you don’t enroll in Medicare, COBRA won’t pay primary claims, and you’ll be stuck with the bills.
Enroll in Medicare during your Initial Enrollment Period. You can keep COBRA if you need it for specific providers or drugs, but don’t rely on it to delay Medicare.
How to Enroll: Step-by-Step Process
Enrolling in Medicare at 65 isn’t complicated. But it does require a few steps, and timing matters.
Here’s how to do it:
Step 1: Confirm you need Medicare at 65.
Are you retired? On an ACA plan? On COBRA? Working for a small employer? If yes to any of these, you need to enroll.
If you’re still working for a large employer (20+ employees), confirm with your HR department whether your coverage is creditable.
Step 2: Choose your path.
You have two main options:
Option 1: Original Medicare + Part D + Medigap
- Enroll in Parts A and B
- Add a Part D drug plan
- Add a Medigap plan (like Plan G or Plan N) to cover your out-of-pocket costs
- Nationwide access to any doctor who accepts Medicare
- No networks, no referrals, no prior authorizations
Option 2: Medicare Advantage
- Enroll in a Medicare Advantage plan that replaces Parts A and B
- Drug coverage is usually included
- Often has $0 premiums and caps your out-of-pocket costs
- Limited to a network of doctors and hospitals
- May require prior authorizations
Not sure which to choose? Read Original Medicare vs. Medicare Advantage and Medicare Advantage vs. Medigap.
Step 3: Submit your application.
You can enroll online at ssa.gov/medicare, by phone (1-800-772-1213), or in person at your local Social Security office.
Start three months before your birthday month to ensure your coverage starts on time.
If you’re already receiving Social Security benefits, you’ll be automatically enrolled in Parts A and B. Your card will arrive in the mail.
Step 4: Add your supplemental coverage.
Once you’re enrolled in Parts A and B, add your Part D plan or Medigap plan. If you’re choosing Medicare Advantage, enroll in that after you’ve enrolled in Parts A and B.
Verify your doctors are in-network, your medications are covered, and your costs fit your budget.
For a detailed walkthrough, read How to Apply for Medicare: Step-by-Step Guide.
What Happens After You Enroll
Once you’re enrolled, you’ll receive your Medicare card in the mail. It will show your Medicare number, your coverage start dates for Part A and Part B, and any other information you need.
Keep that card. Bring it to every doctor’s appointment. And make sure you add your Part D plan or Medigap plan before your coverage starts.
During your first year, you’ll also qualify for a free Welcome to Medicare visit. This is a one-time preventive visit where your doctor will review your health history, check your vitals, and create a prevention plan. It’s covered at no cost — use it.
After your first year, you’ll qualify for an annual Medicare wellness visit. These visits help you stay on top of your health and catch problems early.
Getting Help to Avoid Penalties and Coverage Gaps
You don’t have to figure this out alone.
Medicare has rules. Deadlines. Penalties. And if you get it wrong, you could pay for it for the rest of your life.
Here’s where to get help:
State Health Insurance Assistance Program (SHIP): Free, unbiased counseling from trained volunteers. Find your local SHIP at shiptacenter.org.
Medicare.gov: Official government site with plan comparisons, cost calculators, and enrollment tools.
Licensed, independent Medicare agents: Agents who work for you — not the insurance companies. They’ll walk you through your options, compare plans, and make sure you’re protected.
That’s what we do at Trusted SR Solutions. We help people just like you navigate Medicare without the confusion, the pressure, or the mistakes.
Frequently Asked Questions
How do HSA contributions change once I enroll in Medicare?
You must stop contributing to your HSA the month Medicare starts — including Part A. If you delay enrollment and Part A is retroactive, you could owe tax penalties for contributions made during those months. You can still spend existing HSA funds tax-free on qualified expenses, including Medicare premiums (except Medigap), deductibles, and copays.
Can I delay Part B if I’m volunteering abroad at 65?
No. Volunteering abroad doesn’t count as creditable coverage. If you don’t have qualifying group coverage, you need to enroll during your Initial Enrollment Period or you’ll face lifetime penalties. Consider international health insurance if you’re living abroad, but don’t skip Medicare enrollment.
Do Medicare rules differ for self-employed business owners?
Yes. If you’re self-employed at 65, you’re treated like any worker without large-group coverage. You must enroll in Medicare during your Initial Enrollment Period to avoid penalties and gaps. Your self-employed health insurance doesn’t count as creditable coverage for delaying Medicare.
How does Medicare coordinate with VA care?
Medicare and VA don’t coordinate benefits. You use VA for VA-approved services and Medicare for non-VA providers. Enroll in Medicare Parts A and B at 65 to avoid gaps, penalties, and out-of-pocket costs. If you have Tricare For Life, you need Part B for it to work.
What documentation proves creditable drug coverage before Part D?
Your plan’s Notice of Creditable Coverage letter is proof. Keep annual notices, formularies, ID cards, and premium statements. If your employer plan is creditable, you’ll get this notice every year.
The Bottom Line: Start Early, Get It Right
New to Medicare Turning 65 decisions are some of the most important you’ll make at this stage of life.
But you don’t have to do it alone. And you don’t have to feel overwhelmed.
Start early. Enroll during the three months before your birthday. Confirm whether you need Medicare or whether you can delay. Choose the plan that fits your health, your budget, and your life.
And if you need help, ask. That’s what we’re here for.
Ready to Enroll in Medicare?
If you’re new to medicre turning 65 and you’re not sure what to do next, let’s talk.
We’ll walk through your situation, answer your questions, and help you enroll in the right coverage — without the confusion or pressure.
You can also scan the QR code to fill out your medications, doctors, and pharmacy information ahead of time. That way, we can waive the 48-hour rule and get you answers faster.
Next step is simple: Book your free consultation, or reach out with questions. We’re here to help.
