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Retiring After 65: Moving From Employer Coverage to Medicare

If you worked past 65 with employer insurance, you have a special enrollment window when that coverage ends. Here is how to land smoothly.
A man leaving the office on his last day of work

Your special enrollment period

When you (or your spouse) stop working or lose employer coverage, you get an eight-month window to enroll in Part B without penalty. But drug coverage follows a stricter clock: you have about two months to get Part D coverage in place. Acting in the first month keeps everything seamless.

Watch out for COBRA

COBRA does not count as employer coverage for Medicare’s purposes. Staying on COBRA past 65 without enrolling in Part B can trigger lifelong penalties. This catches many people; do not let it catch you.

The order of operations

Confirm your last day of coverage, enroll in Parts A and B timed to that date, then choose your path (Supplement plus Part D, or Medicare Advantage) so everything starts the day your employer plan ends. We coordinate all three steps routinely.

Retiring soon?
Tell us your last day of work and we will map the exact dates for you.
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