Ask Terry Questions When to enroll in Medicare

When to enroll in Medicare

By Terry Savage on December 01, 2025 | Insurance & Annuities

I watched your podcast on Medicare. Thanks, it was very informative. One question I have that was not brought up. I realize you have a 6 month window (3 months on either side of your 65 birthday) to apply for Medicare but what if you decide to keep working and continue using your employer’s insurance? Does that change the window or do you still make your choices and just delay the start date?

Terry Says

You DO NOT have to sign up for Medicare if you are 65 but still fully covered by your employer’s insurance plan. (Some smaller company plans require Medicare signup as a primary, so check with your company plan.)
And, in fact, you shouldn’t sign up for Medicare if you are contributing to a Health Savings Account. You can no longer contribute once on Medicare — even if you only signed up for the free Part A.

When you DO retire, you get a special enrollment period to sign up for Medicare. Do NOT take COBRA because extending company insurance may penalize you with a late signup fee.

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