RETIRING AFTER 65
Retiring After 65: How to Switch From Employer Coverage to Medicare
Start before the employer plan ends. Parts A and B, Medicare Advantage or Part D, Medigap and a spouse’s coverage can follow different deadlines, so one retirement date may create several separate enrollment tasks.
If you delayed Medicare because you had group health coverage through your or your spouse’s current employment, retirement may give you a Special Enrollment Period for Part B. That does not mean you should wait until the eight-month window is almost over.
Begin by confirming the exact last day of active-employment coverage. Then request the Medicare effective date that avoids a gap, document the employer coverage and arrange the Medicare Advantage, Part D or Medigap coverage you want to begin alongside Medicare.
If you have not yet confirmed that delaying Medicare was safe, start with Can I Delay Medicare If I’m Still Working Past 65?.
START WITH THE END DATE
What Date Does the Employer Coverage Actually End?
Your last day at work and the last day of health coverage are not always the same. Coverage might end on your final workday, at the end of that month or on another date set by the plan.
Ask the benefits administrator to confirm in writing:
- What is the final day of active-employee medical coverage?
- Is the drug coverage creditable through that same date?
- Does retiree coverage begin automatically or require an election?
- Will a spouse or dependent lose coverage on the same date?
- Will the employer complete CMS-L564 promptly?
- Will any HSA contribution be deposited after retirement?
Do not build the Medicare timeline around an assumed end date. A one-day mismatch can affect claims, prescription access or whether a spouse is left uninsured.
THE TWO WINDOWS
Eight Months for Part B Does Not Mean Eight Months for Everything
| Coverage decision | General timing | Why waiting is risky |
|---|---|---|
| Medicare Part B | Generally while current-employment coverage continues or during the eight months after employment or that group coverage ends, whichever comes first | The later months of the SEP can still leave a gap after the employer plan ends. |
| Medicare Advantage or Part D | Generally through two full months after the month employer or union coverage ends | This plan-election window can close well before the Part B SEP. |
| Medigap | Your one-time six-month Medigap Open Enrollment Period begins when you are 65 or older and Part B starts | Starting Part B starts this clock even if other coverage continues. |
| Younger spouse’s coverage | Depends on the option; Marketplace loss-of-coverage enrollment is generally available during the 60 days before and 60 days after the loss | COBRA, a spouse’s employer plan and Marketplace coverage each have separate rules. |
The practical rule: arrange the transition before the employer coverage ends. The eight-month Part B SEP is protection against a penalty for qualifying people; it is not a recommendation to remain uninsured for eight months.
PART A AND PART B
How Do You Apply for Medicare After Working Past 65?
If You Delayed Both Parts A and B
Apply for Medicare through Social Security. If you or your spouse worked for a railroad, contact the Railroad Retirement Board instead. Confirm which proof of current-employment coverage is required.
If You Already Have Part A
Social Security offers an online Part B SEP application. You can also submit CMS-40B together with CMS-L564 and any supporting evidence Social Security requests.
If Railroad Retirement Applies
Railroad beneficiaries generally handle Medicare enrollment through the Railroad Retirement Board. Do not assume the Social Security process and forms are identical.
CMS-40B: your Part B application
CMS-40B is the Application for Enrollment in Medicare Part B. Social Security instructs SEP applicants using the form to state the requested Part B start month in the remarks section. Social Security makes the final effective-date determination.
CMS-L564: proof of employer coverage
CMS-L564 documents the employment and group health plan coverage that support the SEP. The employer normally completes its section. If the employer is unavailable or refuses, contact Social Security about acceptable secondary evidence, such as pay stubs, insurance cards, tax records or explanations of benefits.
Beginning the application about a month before employer coverage ends can help avoid a gap. Processing time can vary, so keep copies of everything submitted and confirm the approved effective date.
HSA CHECK
Stop HSA Contributions Before Medicare Becomes Retroactive
Enrollment in Medicare makes you ineligible to contribute to an HSA. This includes employer contributions. When someone applies for premium-free Part A after 65, Part A can be retroactive for up to six months, but not earlier than the first month of Medicare eligibility.
Medicare therefore advises people working past 65 to stop HSA contributions six months before retiring or applying for Social Security or Railroad Retirement benefits. The exact tax calculation is individual. Read Medicare and HSA Rules: When Should You Stop Contributions? and coordinate the dates with a qualified tax professional.
Retirement can also lower the income Medicare uses to set future premiums. If an older tax return triggers an income-related surcharge after your income has fallen, review how to appeal Medicare IRMAA after retirement with Form SSA-44. Before taking a large distribution or converting retirement funds, see how IRA withdrawals and Roth conversions can affect Medicare IRMAA.
CHOOSE WHAT COMES NEXT
Medicare Is Not Complete When Parts A and B Are Approved
After the Part A and Part B dates are established, decide how you will receive coverage:
Medicare Advantage
A private plan provides Part A and Part B benefits and often includes Part D. Compare networks, prescriptions, prior authorization, copays and the maximum out-of-pocket amount.
Original Medicare and Medigap
Original Medicare can be paired with a Medicare Supplement. Your one-time six-month Medigap Open Enrollment Period begins when Part B starts and you are at least 65.
Prescription Coverage
If you use Original Medicare, review a standalone Part D plan unless you have other creditable drug coverage. Do not compare drug plans by premium alone.
See the complete Medicare Advantage vs. Medicare Supplement comparison and the Medicare Part D guide.
HOUSEHOLD COVERAGE
Do Not Forget the Spouse Who Was Covered Through Your Job
Medicare is individual coverage; there is no family Medicare plan. If retirement ends coverage for a younger spouse, that spouse may need an employer plan, retiree coverage, COBRA, Marketplace coverage or Medicaid. If the spouse is also Medicare-eligible, the spouse must complete a separate Medicare enrollment.
Use What Happens to Your Spouse’s Health Insurance When You Retire and Start Medicare? to plan both sides of the household transition.
RETIREMENT CHECKLIST
A Practical Medicare Transition Checklist
- Confirm the final date of active-employment medical and drug coverage in writing.
- Choose the desired Part A and Part B effective dates and identify the correct enrollment route.
- Obtain CMS-L564 or ask Social Security what alternate proof will be accepted.
- Stop HSA contributions early enough for possible retroactive Part A.
- Compare Medicare Advantage with Original Medicare, Medigap and Part D before the private-plan SEP closes.
- Arrange separate coverage for a spouse or dependent losing the employer plan.
- Keep applications, confirmation numbers, notices and creditable-coverage letters.
- Verify every effective date before cancelling coverage or scheduling care.
COMMON QUESTIONS
Retiring After 65 and Medicare FAQ
Should I wait until my employer coverage ends to apply for Medicare?
Usually, it is better to begin before the coverage ends. Medicare advises people whose employer coverage is ending to sign up about a month earlier. Confirm the requested and approved effective dates with Social Security.
Do I need CMS-40B and CMS-L564?
If you already have Part A and apply for Part B through the working-aged SEP by fax or mail, CMS-40B and CMS-L564 are commonly used. Social Security also offers an online Part B SEP application and decides what documentation is required.
Can my Medicare broker submit Parts A and B for me?
No. Social Security or the Railroad Retirement Board handles Parts A and B. A broker can help you organize timing questions and compare the private coverage choices that begin after Medicare is established.
When does my Medigap Open Enrollment Period begin?
If you are 65 or older, it begins the first month your Part B coverage starts and lasts six months. It is a one-time federal enrollment period, not an annual event.
Can I use COBRA while I wait?
COBRA does not extend the Part B SEP based on current employment. Read the separate COBRA and Medicare guide before relying on it.
WORKING PAST 65 SERIES
Continue the Retirement-to-Medicare Series
These guides divide one complicated transition into separate decisions about delaying Medicare, retiring, HSA contributions, COBRA and a spouse’s coverage.
OFFICIAL INFORMATION
Enrollment resources for retiring after 65
- Medicare.gov: Working past 65
- Social Security: Sign up for Part B only
- Social Security: Part B SEP forms and evidence
- CMS: Application for Enrollment in Part B (CMS-40B)
- CMS: Request for Employment Information (CMS-L564)
- Medicare.gov: Special Enrollment Periods for Medicare Advantage and Part D
- Medicare.gov: When can I buy a Medigap policy?
PLAN THE HANDOFF
Coordinate Medicare Before the Employer Plan Ends
Thompson Medicare Brokerage helps people in Missouri and Illinois compare the Medicare Advantage, Medicare Supplement and Part D choices that follow retirement. We can also help you organize the questions to take to Social Security and the employer benefits administrator.
Social Security or the Railroad Retirement Board determines Parts A and B enrollment and effective dates. The employer or plan administrator confirms job-based coverage and COBRA rights.
Thompson Medicare Brokerage is not connected with or endorsed by the U.S. government or the federal Medicare program. This article provides general educational information. Enrollment rights, effective dates, employer benefits and tax consequences depend on individual facts.