What to review before you turn 65

1. Find out whether Medicare will be automatic

If you are already getting Social Security or Railroad Retirement Board benefits at least 4 months before you turn 65, Medicare generally enrolls you in Part A and Part B automatically. Medicare says your welcome package and card should arrive about 3 months before coverage starts.

If you are not receiving those benefits yet, do not assume Medicare will just happen. You usually need to sign up through Social Security when your enrollment window opens.

2. Mark your Initial Enrollment Period

Your Initial Enrollment Period is the main deadline. It lasts 7 months: the 3 months before your birthday month, your birthday month, and the 3 months after your birthday month.

If your birthday is on the first day of the month, Medicare treats the timing differently for premium-free Part A: coverage starts the month before you turn 65.

3. If you are still working, ask the right questions

Working past 65 is where many Medicare mistakes happen. The key question is whether your coverage comes from current employment for you or your spouse. Retiree coverage, COBRA, Marketplace coverage, and individual coverage do not work the same way.

• Ask HR if you need Part A and Part B at 65. Medicare.gov says job-based insurance might not cover costs if you should have Medicare and do not enroll.
• Ask how many employees the employer has. CMS guidance says if you are 65 or older and covered through current employment, a group health plan generally pays first when the employer has 20 or more employees. If the employer has fewer than 20 and is not part of a qualifying multi-employer group, Medicare generally pays first.
• Ask whether your prescription coverage is creditable. Keep the annual creditable coverage notice. You may need it later to avoid a Part D penalty.

4. Do not use COBRA as your Medicare plan

COBRA can be useful in some health insurance transitions, but it is not the same as active employer coverage for Medicare timing. Medicare.gov warns that if you have COBRA and are eligible for Medicare but not enrolled, COBRA may pay only a small portion of your bills.

If you stop working or lose job-based coverage, your Part B Special Enrollment Period can run even if you choose COBRA. Do not wait until COBRA ends to deal with Part B.

5. Check HSA timing before you enroll

If you or your employer contribute to a Health Savings Account, pause before enrolling in any part of Medicare. Medicare.gov says you and your employer should stop HSA contributions 6 months before you retire or apply for Social Security or Railroad Retirement Board benefits to avoid a tax penalty.

This matters because premium-free Part A can be retroactive up to 6 months when you sign up after 65, but not earlier than the month you became eligible for Medicare.

6. Build your doctor, drug, and pharmacy list

Before comparing plans, write down your doctors, hospitals, prescriptions, dosages, and preferred pharmacies. This is the practical part that keeps the decision grounded.

For 2026, Medicare.gov lists the standard Part B premium as $202.90 per month and the Part B deductible as $283. Part D costs vary by plan, but Medicare says no Part D plan deductible can be more than $615 in 2026, and covered Part D drug out-of-pocket spending reaches catastrophic coverage at $2,100.

7. Compare the two main coverage paths

Original Medicare path

Original Medicare is Part A and Part B. Many people add a standalone Part D drug plan and consider a Medicare Supplement policy, also called Medigap, to help with Original Medicare cost sharing.

Medicare.gov says your one-time Medigap Open Enrollment Period starts the first month you have Part B and are 65 or older. It lasts 6 months. During that window, insurers cannot deny you a Medigap policy because of pre-existing health problems.

Medicare Advantage path

Medicare Advantage is an alternative way to receive Medicare through a private Medicare-approved plan. Many plans include Part D. The tradeoff is that you must review networks, referral rules, prior authorization, copays, and the plan's out-of-pocket limit.

The right answer depends on your doctors, prescriptions, travel habits, budget, risk tolerance, and whether you want the flexibility of Original Medicare with a supplement or the managed-plan structure of Medicare Advantage.

8. Use this final checklist before you choose

• I know my exact Initial Enrollment Period dates.
• I know whether Medicare enrollment will be automatic or whether I need to sign up.
• If I am still working, I checked current-employment coverage, employer size, and whether Part B can safely wait.
• I confirmed whether my drug coverage is creditable.
• I checked COBRA, retiree coverage, Marketplace coverage, or VA/TRICARE rules before making changes.
• I stopped or timed HSA contributions correctly before Medicare starts.
• I compared my doctors, medications, pharmacies, premiums, deductibles, copays, networks, and worst-case costs.
• I know when my Medigap open enrollment window starts if I choose Original Medicare.