Medicare and employer coverage

Keep working. Make a clear Medicare decision.

Turning 65 does not always mean leaving employer coverage. The right timing starts with understanding how your current plan works with Medicare.

Before changing coverage

Who pays first matters

Ask your benefits administrator how the employer plan coordinates with Medicare.

For people eligible because they are 65 or older, a group plan based on current employment generally pays first when the employer has 20 or more employees. With fewer than 20, Medicare generally pays first and the employer plan may require Parts A and B. Multi-employer and other situations can have different rules.

Confirm whether your coverage comes from your or your spouse’s current employment. COBRA and retiree coverage follow different rules and do not protect a Part B delay in the same way.

Review Medicare’s Working-Past-65 Guidance

Talk with your benefits administrator

Compare the full picture

There is no automatic winner. Compare total costs and coverage, not just one premium.

Employer plan

What you have today

Review your share of premiums, deductibles, copays, prescriptions, doctors, and hospitals. Include dental and vision benefits and any coverage for your spouse or dependents. Ask which plan pays first.

Medicare options

What would change

Include Part B and any drug, Advantage, or Medigap premiums, plus expected cost sharing. Check providers, medications, additional benefits, and separate coverage needed for family members.

Explore Medicare Coverage

Enrollment protections

Know your deadlines before you delay

Part B, prescription coverage, and HSA contributions each have their own timing.

Qualifying coverage through current employment may allow you to enroll in Part B while covered or during the eight months after the employment or coverage ends, whichever comes first. COBRA does not extend that window. Confirm a private plan’s separate enrollment deadline too.

Going 63 days or more without Part D or other creditable drug coverage may lead to a drug-plan penalty. Keep your coverage notices and plan a transition before that protection ends.

See Enrollment Periods

Health Savings Accounts

Plan your HSA stop date

You can still use existing HSA funds for eligible expenses after contributions stop.

Once Medicare coverage starts, neither you nor your employer can contribute to your HSA.

Premium-free Part A can begin up to six months before an application made after 65, but not before the month you became eligible. That retroactive start date can make recent HSA contributions ineligible.

Medicare advises stopping HSA contributions six months before retiring or applying for Social Security benefits. If you are newly 65 or have a different enrollment date, confirm the right stop date with your benefits team and a qualified tax professional.

Read the Medicare HSA Guidance

When work or coverage ends

Plan the move to Medicare before your last day

Starting early can help align Medicare with the end of employer coverage.

  1. 1

    Confirm the end date

    Ask when active employment and group health coverage officially end for you and any covered family members.

  2. 2

    Review your enrollment window

    Confirm the Part B Special Enrollment Period and the separate time available for private Medicare coverage.

  3. 3

    Complete required forms

    Ask Social Security whether you need CMS-40B for Part B and CMS-L564 as proof of coverage based on current employment.

  4. 4

    Coordinate the start dates

    Review effective dates before ending other insurance, then compare drug and additional coverage choices.

Complimentary decision workbook

Should I Drop My Employer Coverage for Medicare?

Compare premiums, total costs, doctors, prescriptions, and family coverage. Use the workbook exercises to prepare questions for your benefits administrator and a Licensed Sales Agent.

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Common work and coverage questions

Questions about Medicare and your job

For an age-eligible worker covered through current employment at an employer with 20 or more employees, Medicare Secondary Payer rules generally require the same coverage terms offered to younger workers. Different rules can apply to smaller employers. Ask the benefits administrator about your situation.

Get the right support for your next step

Use these resources alongside your employer benefits information.

Join Medicare education

Attend a live webinar or an in-person classroom session to learn and ask questions.

Explore Upcoming Sessions

Bring us the details of your employer plan.

A Licensed Sales Agent can help compare your Medicare options using your actual costs, providers, prescriptions, and family needs.

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Important Medicare information

MySeniorHealthPlan.com is a private insurance agency and is not affiliated with Medicare or any federal agency. Plan availability varies by area. For information about all of your options, visit Medicare.gov or call 1-800-MEDICARE (1-800-633-4227), TTY: 1-877-486-2048.

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