Age 64 Medicare checklist: what to do in the months before you turn 65

Why start at 64

Your first Medicare sign-up window opens 3 months before the month you turn 65, and your one-time Medicare Supplement window opens with Part B. Starting the year before gives you time to compare without rushing.

Your Age 64 Medicare checklist

1. About 12 months before 65: check your work coverage. If you or your spouse will still have job-based coverage, ask the employer how it works with Medicare. If the employer has fewer than 20 employees, Medicare.gov warns your job coverage might not pay for services unless you have both Part A and Part B.
2. About 6 to 9 months before: write down your dates. Your Initial Enrollment Period is 7 months: 3 months before your birthday month, the month itself, and 3 months after.
3. Get your drug coverage letter. Your current plan must tell you each year whether its drug coverage is creditable. Going 63 days or more without Part D or creditable coverage can add a lifelong penalty.
4. If you have an HSA, ask your plan or tax advisor when to stop contributions. Premium-free Part A can be backdated up to 6 months, but not earlier than the month you turned 65.
5. About 3 months before: sign up for Part A and Part B (unless you are delaying Part B for job-based coverage). Sign up before your birthday month and Part B starts the month you turn 65. If you already get Social Security benefits, you are usually enrolled automatically.
6. Compare Medicare Supplements. Your 6-month Medigap Open Enrollment Period starts the first month you are 65 or older and have Part B. Companies can't turn you down or charge more for health problems during it. Plan letters are standardized, so compare Plan G vs. Plan N.
7. Choose drug coverage to go with your supplement, since Medigap policies generally don't cover prescriptions.
8. Set a yearly reminder. Oklahoma's birthday rule may let you change supplements each year.

More turning-65 guides: Medicare at 65 in Oklahoma · Age 64 Medicare checklist · Yukon · Mustang · Moore · Norman · Guthrie · Piedmont · Deer Creek · Midwest City

Sources (checked Oct 30, 2026): Medicare.gov: When does Medicare coverage start? · Medicare.gov: When can I sign up for Medicare? · Medicare.gov: Medigap Open Enrollment Period · Medicare.gov: Avoid late enrollment penalties · Medicare.gov: Creditable prescription drug coverage

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