Turning 65 is not just another birthday. It is when many people first become eligible for Medicare, compare coverage paths and coordinate retirement decisions.
The exact order depends on whether you are still working, have employer coverage, contribute to an HSA or already receive Social Security. This checklist helps organize the decisions that matter most.
Start three to six months before 65
Review your current health coverage, expected retirement date and whether Medicare will become primary. If you are already receiving Social Security benefits, confirm whether Parts A and B will begin automatically. Otherwise, you will generally apply through Social Security.
- Write down your birthday month and desired coverage date
- Ask how employer coverage coordinates with Medicare
- Review HSA contributions before Medicare begins
Gather the details that affect your coverage
A Medicare comparison is most useful when it reflects your actual healthcare—not a generic brochure.
- Doctors, specialists and preferred hospitals
- Prescription names, dosages and pharmacies
- Travel needs, budget and preference for predictable costs
Choose a coverage path
After Parts A and B, the central decision is whether to keep Original Medicare and add Medigap plus Part D, or receive your Medicare benefits through a Medicare Advantage plan. These are different paths and are not used together.
- Compare Plan G and Plan N if considering Medigap
- Check networks and plan rules for Medicare Advantage
- Do not overlook prescription drug coverage
Protect the important enrollment windows
Your one-time federal Medigap Open Enrollment Period begins the first month you are 65 or older and enrolled in Part B and lasts six months. Part D and Part B also have separate timing rules, so confirm every effective date before existing coverage ends.