If you’re over 65 and planning to retire within six months, timing your Medicare enrollment correctly is crucial to avoid gaps in coverage and penalties. When you have employer coverage through your own job, you can delay Medicare enrollment past 65 without penalty, but you must act within eight months after your employment ends or your employer coverage stops, whichever comes first.
Contact Social Security three months before retiring to ensure smooth enrollment in both Part A and Part B. Even if you plan to use COBRA or retiree coverage, you should still enroll in Medicare Parts A and B to avoid future complications. Part A is typically premium-free if you have 40 quarters of work history, while Part B costs $202.90 monthly in 2026.
If your spouse is retiring and you’re covered under their employer plan, the same eight-month window applies from when their coverage ends. Missing this deadline triggers a 10% penalty for each full 12-month period you delayed Part B enrollment, applied permanently to your monthly premium.
For those still working past 65, you can keep just Part A if your employer has 20 or more employees, as their coverage remains primary.