Chaperone Health Insurance Plus
Turning 65 Medicare Checklist
Reviewed October 2026
Turning 65 brings a short list of Medicare decisions with firm deadlines, and the order you handle them in matters. I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. I’ve spent the last 8 of my 14 years in insurance focused on Medicare, and I built this turning 65 checklist to show what to do and when, starting about six months before your 65th birthday and continuing through the months after.
If you’d like the bigger picture first, including how I help people retiring from a job or leaving employer coverage, see my Turning 65 or Retiring page. This guide is the step-by-step version. Work through it at your own pace, and when you want help applying it to your situation, book a free plan review. I’ll get back to you personally within 24 to 48 hours.
I’LL EVEN CALL YOUR DOCTOR
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The rules are the same for everyone, but the right dates depend on you, so before I recommend anything, I check:
- Your personal timeline: your birthday, your work situation, and any employer coverage or HSA
- Your doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
- Your full-year cost, not only the premium
If anything is unclear, I call your doctor’s office to confirm it. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.
Hear how I help you choose a plan with confidence.
MORE THAN A FREE QUOTE
Why Choose Me When You’re Turning 65
When you’re comparing Medicare agents before your 65th birthday, here’s what to look for, and what you can expect from me.
A Personal Timeline, Not a Generic One: I start with your birthday, your work situation, and your current coverage, and lay out exactly which months to act in, so nothing starts late and nothing overlaps.
Your Doctors, Hospitals, and Prescriptions Checked First: Before I recommend any plan, I check your doctors, hospitals, and every prescription against its network and drug list, including your pharmacy. If something is unclear, I’ll call your doctor’s office myself.
Every Question Answered, at Your Pace: Medicare has a lot of moving parts, and most people spend less than an hour choosing a plan. I take as long as you need, explain each piece in plain language, and answer every question until it makes sense. There’s no pressure and no obligation to enroll.
The Plan That Costs Less for You: The lowest premium isn’t always the lowest cost. I calculate your full-year cost for every plan, including copays, drug costs, and your out-of-pocket maximum, based on your health needs, before you choose.
My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly, so you get personal guidance and ongoing support at no additional charge.
Both Paths, Side by Side: Medicare Advantage, Medigap, and Part D each work differently. I lay out every path that fits your situation and explain what you’d gain and give up with each, so you decide with the full picture.
I Handle the Paperwork: If you choose a plan, I complete the application with you, confirm your enrollment window, and follow it through to approval, so the process is as simple as a conversation.
Licensed and Verified: I’m licensed in 33 states, I complete AHIP’s annual Medicare certification, and I’m certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.
I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, on Zoom, or at your home in Broward, Miami-Dade, or Palm Beach, and I reply within 24 to 48 hours. I help 75 to 80 new Medicare clients each year, based on my own client records, and I review your coverage every Annual Enrollment Period and help with claims and billing in between.
You can read all 25 reasons we should work together on my Why Choose Me page.
Turning 65: What Do I Need to Do Six Months Before My Birthday?
Six months out is the planning stage. Nothing has to be filed yet, but these steps set up every decision that follows, and they make a good Medicare checklist to start with.
Mark Your Initial Enrollment Period: Your Initial Enrollment Period is seven months long: the three months before your birthday month, your birthday month, and the three months after. Write those months on your calendar now. If your birthday falls on the first of the month, your dates shift one month earlier.
Find Out Whether You’ll Be Enrolled Automatically: If you’re already getting Social Security or Railroad Retirement benefits at least four months before you turn 65, you’ll usually be enrolled in Part A and Part B automatically, starting the first day of your birthday month. If you aren’t collecting benefits yet, nothing happens on its own. You’ll need to sign up yourself.
Talk to Your Employer or Benefits Office: If you or your spouse are still working, ask three questions. How many employees does the employer have? Will the group plan pay first or second once you’re eligible for Medicare? Is its drug coverage “creditable,” meaning it’s expected to pay at least as much as standard Medicare drug coverage? With 20 or more employees, your job-based plan generally pays first, and many people delay Part B. With fewer than 20, Medicare usually pays first, and you generally need both Part A and Part B. My guide to CMS-L564 and CMS-40B forms explains what to file when you sign up for Part B later.
Plan Your HSA Contributions: You can’t contribute to a Health Savings Account once any part of Medicare starts, including Part A. If you sign up for Part A after 65, it’s usually backdated up to six months (but not before the month you turned 65), so many people stop contributions about six months before they apply. Collecting Social Security also enrolls you in Part A. I can’t give tax advice, so confirm your HSA timing with your tax professional or HSA administrator.
Create Your my Social Security Account: You’ll use it to apply online, check your application, and see your benefit information. My guide on how to apply for Medicare online walks you through setting it up, starting with Login.gov.
Three Months Before: Apply During Your Initial Enrollment Period
Your Initial Enrollment Period opens three months before your birthday month. For most people, this is the best time to apply, because signing up before your birthday month lets Part B start in your birthday month, with no gap. If you sign up during your birthday month or the three months after, Part B starts the month after you sign up.
If You’re Enrolled Automatically: Your Medicare card usually arrives about three months before your birthday, along with instructions. Part B has a monthly premium, so if you have qualifying coverage through current employment and want to delay Part B, follow the instructions in that package to decline it. Keep the card somewhere safe.
If You Need to Sign Up: Apply through Social Security, online at ssa.gov, by phone at 1-800-772-1213 (TTY 1-800-325-0778), or at a local Social Security office. Applying online is often the quickest. You’ll need your Social Security number, your place of birth, and the start and end dates of any current group health coverage.
If You’re Still Working and Delaying Part B: Many people still sign up for Part A, since most people don’t pay a premium for it if they or their spouse worked and paid Medicare taxes long enough, usually about 10 years. If you have an HSA, read the HSA step above first, because Part A ends your ability to contribute. When your job or the coverage ends, you’ll have an eight-month Special Enrollment Period to sign up for Part B. That window starts when the job or coverage ends, even if you pick COBRA, so COBRA alone doesn’t protect you from the Part B penalty. My guide to COBRA and Medicare at 65 explains the timing.
Start Comparing Coverage: Once you’ve applied, you can join a Medicare Advantage or Part D plan during the same Initial Enrollment Period. Choosing during the three months before your birthday month lets that coverage start when your Medicare does.
Your Birthday Month: Original Medicare With Medigap and Part D, or Medicare Advantage
By your birthday month, most people are choosing between two paths. Each one works very differently, so I walk every client through both.
Original Medicare, Medigap, and Part D: You keep Original Medicare, which is Part A (hospital insurance) and Part B (medical insurance), and add a Medicare Supplement (Medigap) plan to help pay costs Original Medicare leaves behind, such as deductibles and coinsurance. Medigap plans sold today don’t include drug coverage, so most people add a standalone Part D plan. You can see any doctor or hospital in the country that accepts Medicare, but you’ll pay separate premiums for each piece.
Medicare Advantage (Part C): These plans are offered by private insurance companies approved by Medicare. They’re a different way to get your Part A and Part B benefits, not a supplement to Original Medicare, and many include drug coverage. Most use provider networks, and each plan has its own costs, network, and extra benefits, which can change every year. You can’t use a Medigap plan with a Medicare Advantage plan.
The right path depends on your doctors, your prescriptions, how often you travel, and how much cost you’d prefer to pay up front versus when you get care. Before you choose, I check your doctors and hospitals, including HCA Florida, Memorial Healthcare System, and Baptist Health, against each plan, and run every prescription through each drug list. If you’re comparing drug coverage, my Medicare Part D page explains how it works.
After You Turn 65: Protect Your Medigap Window and Avoid the Part D Penalty
The months after your birthday hold two deadlines that are easy to miss, because nobody sends you a reminder.
Your Medigap Open Enrollment Period: You get a one-time, six-month Medigap Open Enrollment Period that starts the first month you’re 65 or older and enrolled in Part B. During those six months, you can buy any Medigap policy an insurer sells in your area, and it can’t turn you down or charge you more because of your health. After it ends, insurers may use medical underwriting, which means they can ask health questions and may decline your application, except in certain situations where you have guaranteed issue rights. If you’re delaying Part B because you’re still working, this window waits until you sign up for Part B.
The Part D Penalty: If you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period ends, Medicare may add a late enrollment penalty to your drug premium for as long as you have Part D. It’s 1% of the national base beneficiary premium for each full month you went without coverage. For 2027, that base premium is $41.33. People who get Extra Help don’t pay this penalty.
The Part B Penalty: If you didn’t sign up for Part B when you were first eligible and don’t qualify for a Special Enrollment Period, your Part B premium can go up 10% for each full 12-month period you could have had it, usually for as long as you have Part B.
Keep Your Creditable Coverage Notices: If you’re relying on employer or union drug coverage, the plan generally has to send you a notice each year, before October 15, saying whether that coverage is creditable. File every notice you get. If you join Part D later, it’s your proof that you didn’t need to enroll sooner.
Check Your First Statements: Once your coverage starts, make sure your Medicare card, your plan’s member ID card, and your first bills match what you chose. If something looks wrong, call me and I’ll help sort it out.
What to Gather for Your Medicare Checklist
Having these ready before you apply and before we compare plans saves time and catches problems early.
For Your Application: Your Social Security number, your place of birth, your my Social Security account login, and the start and end dates of any group health coverage you’ve had since 65. If you’re signing up for Part B after employer coverage ends, also have Form CMS-40B and Form CMS-L564 (or other proof of your job-based coverage).
For Comparing Plans: A list of your doctors and specialists, the hospitals you’d want to use, every prescription with its dose and how often you fill it, and the pharmacy you use. Add any upcoming procedures or ongoing treatment, and how much you travel outside South Florida.
From Your Current Coverage: Your employer plan’s summary of benefits, your creditable coverage notice, any COBRA paperwork, and your HSA balance and contribution details.
For Your Household: Medicare covers one person at a time. If your spouse is younger than 65 and was on your work plan, they’ll need their own coverage. I also help with individual and family health plans, so I can plan for both of you.
Browse the Knowledge Base
Enrollment and Timing
MORE WAYS I CAN HELP
Find the Right Coverage for Every Stage of Life
Most households need more than one kind of coverage, and what you need changes as life does. Keep reading for the details on this page, or see all the coverage I help with and my guides to each type of insurance:
Frequently Asked Questions About Turning 65 and Medicare
When Should I Sign Up for Medicare When Turning 65?
If you don’t have job-based coverage from current work, sign up during the three months before your birthday month. That lets Part A and Part B start the first day of your birthday month. You can still sign up during your birthday month or the three months after, but Part B will start the month after you apply. If you’re already collecting Social Security at least four months before you turn 65, you’ll usually be enrolled automatically.
I’m Turning 65 and Still Working. Do I Have to Sign Up for Medicare?
It depends on your employer’s size and your coverage. If your employer has 20 or more employees and you’re covered through current work, you can usually delay Part B without a penalty and sign up later during an eight-month Special Enrollment Period. If your employer has fewer than 20 employees, Medicare usually pays first, so you generally need Part A and Part B at 65. Ask your benefits office how its plan works with Medicare, and see my guide to the CMS-L564 and CMS-40B forms for signing up later.
Will I Be Enrolled in Medicare Automatically?
Only if you’re already getting Social Security or Railroad Retirement benefits at least four months before your 65th birthday. In that case, your card usually arrives about three months before your birthday, along with instructions for keeping or declining Part B. If you aren’t getting benefits yet, you need to apply through Social Security.
What Happens if I Miss My Initial Enrollment Period?
If you don’t qualify for a Special Enrollment Period, you may have to wait for the General Enrollment Period, January 1 to March 31, to sign up for Part B, with coverage starting the month after you sign up. You may also pay a Part B late enrollment penalty of 10% for each full 12-month period you went without it, and a separate Part D penalty if you went 63 days or more without creditable drug coverage. Both penalties usually last as long as you have that coverage.
Does My Spouse Get Medicare When I Turn 65?
No. Medicare covers each person individually, so your spouse qualifies based on their own age or disability. If your spouse is under 65 and was covered by your work plan, losing that plan usually opens a Special Enrollment Period for a Marketplace plan. I can help with both your Medicare and your spouse’s coverage.
Is Medicare Only for People Turning 65?
No. People under 65 may qualify because of a disability, End-Stage Renal Disease, or ALS. The timeline in this guide is built around turning 65, but I also help people who qualify earlier.
Do You Offer Every Medicare Plan in My Area?
No. We do not offer every plan available in your area. Currently we represent 8 organizations which offer 65 products in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY users should call 1-877-486-2048), 24 hours a day, 7 days a week, to get information on all of your options. In Florida, you can also get free Medicare counseling through the state’s SHIP program, called SHINE.
Book a Free Plan Review
Turning 65 soon? Pick a time for a free 15-minute call by phone or video, and I’ll map out your enrollment timeline with you. My help never costs you anything extra.
Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309
Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.
- How It Works
How we'll work together
Five steps, no pressure, and I stay with you after you enroll.
1
We talk about you
By phone, Zoom or face to face. Your health, your budget, your doctors.
2
I check the details
Doctors, hospitals, prescriptions and pharmacy, checked against each plan.
3
We compare real costs
A full-year estimate for each option, explained in plain language.
4
You decide, I enroll you
No pressure. If you choose a plan, I handle the application with you.
5
We review every year
Plans and networks change. I check yours each year and help with claims in between.