Medicare
A month-by-month Medicare checklist, from 3 months before your 65th birthday to 3 months after. Your HBS advisor can walk through it with you at no cost.
Turning 65 and wondering what you need to do? Most people sign up for Medicare Part A and Part B during a 7-month enrollment window around their 65th birthday. Then, they decide how to get coverage beyond Original Medicare.
This turning 65 checklist explains when to sign up for Medicare, when coverage starts, which late enrollment penalties may apply, and what to consider if you’re still working.
If you live in Pennsylvania, you can also learn about state programs that may help with prescription costs and Medicare counseling.
At HBS, our licensed advisors compare coverage from local and national carriers at no cost to you. We help you compare your options and choose coverage that fits your needs and budget. Learn how a local Medicare broker can help you understand your Medicare options.
- What’s required: Know when and how to enroll in Medicare.
- What’s optional: Compare coverage options beyond Original Medicare.
- What’s Pennsylvania-specific: Learn about PACE/PACENET and available state Medicare counseling.
When to sign up for Medicare: your 7-month window
Your Medicare Initial Enrollment Period lasts 7 months. It starts 3 months before the month you turn 65 and ends 3 months after your birthday month.
For example, if you turn 65 in July, your enrollment window runs from April through October.
If you receive Social Security benefits at least 4 months before turning 65, you automatically get Medicare Part A and Part B. Otherwise, sign up through the Social Security Administration (SSA).
When you apply, have your Social Security number, place of birth, and the start and end dates of your current and post-65 group health plans ready. Apply through the SSA Medicare sign-up page, or call 800-772-1213.
If You Have a Health Savings Account
If you have a Health Savings Account (HSA), stop contributing 6 months before you retire or apply for Social Security benefits. Talk with your HBS advisor early to review your Medicare enrollment timing.
Your turning 65 checklist: month by month
Use this turning 65 checklist to plan your Medicare enrollment around your birthday month. Follow each step to understand what to do and when.
3 Months Before Your Birthday Month
Sign up for Medicare Part A and Part B if you aren’t enrolled automatically. Signing up during this period means coverage starts the month you turn 65.
Gather the information the Social Security Administration (SSA) needs:
- Your Social Security number
- Your place of birth
- The start and end dates of your current and post-65 group health plans
Book a review with HBS to compare your Medicare coverage options before your birthday month.
2 Months Before Your Birthday Month
Compare your coverage options with your HBS advisor. You can choose Original Medicare with a Medicare Supplement (Medigap) policy and a Part D prescription drug plan, or a Medicare Advantage plan.
List your prescriptions, pharmacies, and doctors. Your advisor can check them against the options you’re considering.
1 Month Before Your Birthday Month
- Check that your Medicare card has arrived. The SSA mails your card 3 months before your Medicare coverage starts.
- Confirm your Medicare Part A and Part B start dates.
- Apply for your Medigap, Part D, or Medicare Advantage coverage based on the option you’ve chosen with your advisor.
Your Birthday Month
Check your Medicare coverage start date. If you signed up before your birthday month, coverage starts this month. Coverage always starts on the first of the month. If you sign up during your birthday month or any of the following 3 months, coverage starts the next month.
Remember that premium-free Part A starts the month you turn 65. If your birthday falls on the first of the month, Part A starts the month before.
1 Month After Your Birthday Month
Book your free Welcome to Medicare preventive visit. You can receive this visit once during your first 12 months of Part B. It is not a comprehensive physical exam. You pay nothing if your provider accepts assignment.
2 Months After Your Birthday Month
- Check that your first premiums and plan ID cards have arrived.
- Confirm that your pharmacy has your new prescription drug plan information.
3 Months After Your Birthday Month
Review your enrollment status. This is the final month of your 7-month Initial Enrollment Period.
Check your Medigap enrollment window if you’re considering a Medicare Supplement policy. Your one-time 6-month Medigap Open Enrollment Period starts when you are 65 or older and have Part B. During this period, insurers can’t use medical underwriting. This window does not repeat every year.
Note the Annual Enrollment Period, which runs from October 15 through December 7. Learn more about your annual plan review with HBS.
When does Medicare coverage start?
Your Medicare coverage start date depends on when you sign up during your Initial Enrollment Period.
| When you sign up | When coverage starts |
|---|---|
| Before the month you turn 65 | The month you turn 65 |
| During the month you turn 65 | The next month |
| During the 3 months after your birthday month | The next month |
- Medicare coverage starts on the first day of the month.
- If your birthday falls on the first of the month, premium-free Medicare Part A starts the month before you turn 65.
For details, read Medicare.gov’s guide to when Medicare coverage starts.
Late enrollment penalties to avoid
Medicare late enrollment penalties depend on your coverage history and when you enroll.
- Part B: If you could have enrolled in Medicare Part B but did not, you may pay a penalty. It adds 10% for each full 12-month period you were eligible but went without Part B. The penalty usually lasts as long as you have Part B.
- Part D: If you go 63 days or more without creditable prescription drug coverage after becoming eligible, you may pay a penalty. It adds 1% for each month you went without creditable coverage. The penalty usually lasts as long as you have Part D.
Before delaying Part B or prescription drug coverage, ask your HBS advisor to review your enrollment timing and existing coverage.
For the official rules, read Medicare.gov’s guide to avoiding late enrollment penalties.
Still working at 65?
If you or your spouse has health coverage through current employment when you turn 65, you may be able to delay Medicare Part B without a late enrollment penalty.
When that job-based coverage ends, you generally have an 8-month Special Enrollment Period to sign up for Part B.
COBRA and retiree coverage do not count as coverage from current employment for this rule. Do not wait for COBRA coverage to end before enrolling in Part B.
If your employer has fewer than 20 employees, ask how Medicare affects your job-based coverage before delaying Part B.
Read our guide to working past 65 for more details about Medicare enrollment deadlines and employer coverage.
Help for Pennsylvanians
Pennsylvania residents turning 65 can check state resources for prescription assistance and Medicare counseling.
PACE and PACENET
PACE and PACENET help eligible Pennsylvania residents pay for prescription drugs. You must be at least 65 and have lived in Pennsylvania for at least 90 days. Income limits apply, and these programs work alongside Medicare Part D.
Call 1-800-225-7223 to ask about eligibility and enrollment. For current income limits and program details, visit the official Pennsylvania PACE and PACENET information page.
You can also learn more through HBS’s guide to PACE and PACENET prescription help.
PA MEDI
PA MEDI offers free, confidential Medicare counseling through Pennsylvania’s state program. It does not sell or recommend insurance products or brokers.
Call 1-800-783-7067 for counseling. The service is available Monday through Friday, from 8 a.m. to 5 p.m.
What to have ready
Before your Medicare review with HBS, gather these details so your advisor can review your enrollment timing and coverage options with you.
- Social Security number
- Birthplace: City and state
- Current or recent group health plan dates: Start and end dates for your current and post-65 coverage, if applicable
- Prescription list: The names of your current prescription medications
- Doctors and pharmacies: The doctors you see and the pharmacies you use
- Health Savings Account (HSA) details: Whether you have an HSA and relevant contribution information
Bring these details to your review with your HBS advisor. They can help you discuss your Medicare enrollment timing and coverage options.
Who you’d be working with
Common questions
Is Medicare enrollment automatic at 65?
Medicare enrollment is automatic at 65 if you receive Social Security benefits at least 4 months before turning 65. If you do not receive benefits that far in advance, you generally need to sign up through Social Security. You can apply through the Social Security Administration or call 800-772-1213.
When should I sign up for Medicare?
Sign up during your 7-month Initial Enrollment Period. It starts 3 months before the month you turn 65 and ends 3 months after your birthday month. If you sign up during the 3 months before your birthday month, your Medicare coverage starts the month you turn 65.
What happens if I sign up late?
Late enrollment penalties may apply if you miss the applicable enrollment deadlines. Part B adds 10% for each full 12-month period you could have enrolled but did not. Part D adds 1% for each month you go without creditable prescription drug coverage after 63 days. These penalties usually last as long as you have the coverage.
Do I need Part B if I’m still working?
Not necessarily. You may be able to delay Part B without a penalty if you or your spouse has health coverage through current employment. Employer size matters, too. Employers with fewer than 20 employees may require you to have Medicare Part A and Part B. Review your situation with your HBS advisor before delaying enrollment.
When can I buy a Medigap policy without health questions?
Your one-time 6-month Medigap Open Enrollment Period starts when you are 65 or older and have Medicare Part B. During this period, insurers cannot use medical underwriting. This period does not repeat every year, so review your enrollment timing before choosing a Medicare Supplement policy.
Does HBS charge for a turning-65 review?
No. Carriers compensate us directly, so your premium is the same whether you work with us or enroll on your own. Your HBS licensed advisor can compare your options and help you understand the coverage choices available to you.
Book your turning-65 review
Turning 65 does not mean you have to figure out Medicare on your own.
Book a turning-65 review with HBS. Your licensed advisor can walk through your enrollment timeline, coverage options, doctors, prescriptions, and questions with you. The same advisor can help you before your birthday and every year after, at no cost to you.
Call 412-865-3200 to speak with HBS.
