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Coastal Georgia and the South Carolina Lowcountry, plus 9 further states by phone or video.

Medicare · 18 March 2026 · 6 min read

Still working at 65? Employer cover and Medicare

Whether you can safely delay depends on one thing: how many employees your employer has.

By Desmond Okoye, Cedar Landing Benefits

Professional black woman smiling at desk using laptop and smartphone in office.

Working past 65 is now normal, and the Medicare rules have not caught up with how confusing that makes things. The good news is that the decision turns on a single question.

How large is the employer whose plan covers you?

Twenty employees is the line

If the employer has twenty or more employees, its plan generally pays first and you can delay Part B without penalty while that active employment continues. If it has fewer than twenty, Medicare usually pays first — and delaying Part B can leave you with very little real cover, because the group plan pays as though Medicare had already paid.

That second case surprises people badly. Ask your HR department which applies, in writing, and keep the answer.

What protects you and what does not

Active employment protects a delay. COBRA does not. Retiree coverage does not. When employment ends, an eight-month special enrolment period opens for Part B and a shorter one for drug cover — and taking COBRA does not extend it.

If you contribute to a health savings account, stop six months before you enrol or claim Social Security, because Part A can backdate.

Often worth taking Part A anyway

Premium-free Part A can usually be taken at 65 without disturbing an employer plan, unless you are contributing to an HSA. It costs nothing and covers a hospital stay the group plan may handle less generously.

The exception really matters though: if you want to keep contributing to an HSA, taking Part A ends that.

An estimate for planning, not a quote. Medicare and the Marketplace set your real figures.

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