DailyGlimpse

Navigating Medicare at 65: Why the Size of Your Employer Matters

AI
April 29, 2026 · 2:18 PM

Turning 65 and still working? The number of employees at your company determines whether you can delay Medicare without penalty. Here's what you need to know about the 20-employee rule, special enrollment periods, and common pitfalls.

For workers at companies with 20 or more employees, employer coverage remains primary, and you can delay Medicare Part B without incurring late enrollment penalties. You'll get a Special Enrollment Period when you eventually retire or lose coverage. But if your employer has fewer than 20 staff, Medicare becomes primary, and delaying Part B can trigger permanent penalties.

Federal employees with FEHB coverage have additional coordination rules. Self-employed individuals must carefully evaluate their options as they may lack employer-sponsored insurance. Veterans with VA benefits should note that VA coverage does not count as creditable drug coverage for Medicare Part D, potentially leading to penalties if they delay.

One critical trap: Health Savings Account (HSA) contributions must stop six months before enrolling in Medicare Part A or B, as Medicare rules prohibit HSA contributions after enrollment. Failure to stop contributions can trigger IRS penalties.

Knowing these rules can save retirees thousands in unnecessary premiums and penalties. Always review your specific situation with a benefits advisor.