Retiring After 65?

Over 65 & Retiring Soon? Here’s What to Do

If you delayed Medicare because you or your spouse had current employer coverage, retiring creates a Special Enrollment Period. In most cases, you can sign up for Part B any time while still covered by the employer plan, or within 8 months after the employment or employer coverage ends—without a late-enrollment penalty.

There are generally two steps:

1. Enroll in Medicare Part B (and Part A too, if you don’t already have it).
If you’re retiring soon, don’t wait until after coverage ends to start the process. Medicare says the 8-month Special Enrollment Period begins when you stop working or lose the employer coverage, and that timing is important to avoid gaps or penalties.

2. Choose the coverage that will go with Medicare.
Once you move off employer insurance, you’ll usually need to decide how you want Medicare to work going forward—such as Original Medicare with other coverage options or a Medicare Advantage plan. The right fit depends on your doctors, prescriptions, budget and preferences.

Important reminders

  • Don’t assume COBRA solves the problem. Medicare says the 8-month Special Enrollment Period still starts when employment or employer coverage ends, even if you elect COBRA.

  • If you have an HSA, plan carefully. Social Security notes that Medicare coverage can affect HSA contribution eligibility, including retroactive Part A in some situations.

  • Start early. The safest move is to begin the Medicare process before your employer plan ends.

Retiring after 65 and not sure what to do next?
I can help you understand the timing, enrollment steps and coverage options before your employer insurance ends.

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