He Thought COBRA Would Buy Him Time. It Didn't.

The Assumption That Cost Him

When Robert left his job at 66, HR offered him COBRA to bridge the gap. He took it, assumed he had time, assumed Medicare could wait until COBRA ran out. It couldn’t. COBRA and retiree coverage don’t count as active employer coverage for Medicare’s Special Enrollment Period, and by the time he found out, his enrollment clock had already been running for months.

Leaving a job soon, or already relying on COBRA? Don’t assume, confirm your actual enrollment window

It Depends on Employer Size

20+ employees: group coverage is typically primary, Part B can usually be delayed penalty-free, with an 8-month SEP once employment or coverage ends.

Fewer than 20 employees: Medicare typically becomes primary at 65, meaning enrollment is usually required right away, even while still working.

The HSA Trap

Contributing to a Health Savings Account? You must stop contributing 6 months before enrolling in Medicare or Social Security, since Part A applies retroactively up to 6 months. Miss this, and a tax penalty follows.

Still working, still confused about what applies to you? Get your specific work situation reviewed before you decide

Does COBRA Let Me Delay Medicare?

No. This is the mistake Robert made. COBRA and retiree coverage do not extend your Special Enrollment Period.

Should I Take Part A With an HSA?

Worth a real conversation with both a tax professional and a Medicare advisor before deciding, since Part A’s retroactive nature can interfere with HSA eligibility even if Part B is delayed.

Employer Has Fewer Than 20 Employees?

Enroll during your Initial Enrollment Period like anyone else, and coordinate with HR on how coverage will work together going forward.

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