SeniorSenseGuide

Planning for myself

Turning 65? Your Medicare Decision Timeline

What to check before 65, when Medicare enrollment usually opens, when delaying Part B may be legitimate, and the mistakes that can create penalties or coverage gaps.

Last reviewed: August 11, 2026Educational guidance — not individualized legal, tax, medical, or financial advice
Start here

For most people, Medicare eligibility begins at 65 and the Initial Enrollment Period generally spans seven months. Do not wait for the birthday month to begin reviewing current coverage.

01

Start 3–4 months before 65

For most people, Medicare eligibility begins at 65 and the Initial Enrollment Period generally spans seven months. Do not wait for the birthday month to begin reviewing current coverage.

02

Inventory your current coverage

Identify whether coverage is based on your own current employment, a spouse’s current employment, retiree coverage, COBRA, Marketplace coverage, TRICARE, VA benefits, or another arrangement. Medicare treats these differently.

03

If you are still working

Some people with qualifying group health coverage based on current employment can delay Part B and use a Special Enrollment Period later. COBRA is not treated the same as active-employment coverage for this purpose.

04

Watch HSA timing

If you work past 65 and contribute to an HSA, coordinate Medicare enrollment carefully. Premium-free Part A may start retroactively for up to six months when you enroll after 65, but not earlier than the month you became eligible. Consider the effect on HSA contribution eligibility before applying.

05

Compare coverage paths

Once Parts A and B are settled, compare Original Medicare—often with Part D and possibly Medigap—with Medicare Advantage. Compare doctors, prescriptions, annual out-of-pocket exposure, travel needs, and authorization rules, not just premiums.

06

Use free counseling when the choice is unclear

State Health Insurance Assistance Programs provide free Medicare counseling to beneficiaries, families, and caregivers.

PRIMARY SOURCES

Where this guidance comes from

Rule-sensitive guides prioritize government and other primary sources. Links open the official source in a new tab.

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