Turning 65: your Medicare checklist
What to do, and when, so nothing falls through the cracks.
Most Medicare mistakes happen around 65, and most of them come from timing rather than choosing the wrong plan. This checklist walks you through the months before and after your birthday.
6 months before
- Look up your Initial Enrollment Period with our calculator.
- If you're working, ask your benefits office how its plan works with Medicare and whether the employer has 20 or more employees.
- If you contribute to an HSA, plan to stop contributions up to 6 months before you'll apply for Medicare (Part A can be backdated up to 6 months).
- List your doctors, prescriptions and pharmacies; you'll need them to compare plans.
3 months before
- If you're not getting Social Security benefits, apply for Medicare through Social Security now so coverage starts on time.
- If you're enrolled automatically, watch for your card. Decline Part B only if your job-based coverage lets you delay safely.
- Decide between Original Medicare (with a drug plan and possibly Medigap) and a Medicare Advantage plan.
Your birthday month
- Make sure you've joined a drug plan or have other creditable drug coverage, or a penalty may apply later.
- If you want Medigap, your 6-month Medigap Open Enrollment Period starts the month your Part B starts (at 65 or older). This is the best time to buy.
- Schedule your Welcome to Medicare preventive visit within your first 12 months of Part B.
After
- Keep proof of any job-based coverage you used to delay Part B.
- Mark October 15 to December 7 each year to review your plans.
- Read your plan's Annual Notice of Change every September.
- If your income dropped because you retired, you may be able to lower an IRMAA surcharge with form SSA-44.
Common questions
You'll be enrolled in Parts A and B automatically, but you still need to choose drug coverage and decide on Medigap or Medicare Advantage.
During your 6-month Medigap Open Enrollment Period, which starts the month your Part B starts. Insurers can't use your health to deny you or charge you more then.
Want help with your own choices?
Every state runs a State Health Insurance Assistance Program (SHIP) with trained counselors who give free, unbiased Medicare help and do not sell plans. Find yours on our Medicare by state pages, or call Medicare at 1-800-MEDICARE (1-800-633-4227) (TTY 1-877-486-2048, 24 hours a day, 7 days a week).
Planning the rest of your coverage in retirement? We can help with life insurance later in life and final expense coverage.
Sources
- When does Medicare coverage start?, Medicare.gov. Checked September 29, 2026.
- Working past 65, Medicare.gov. Checked September 29, 2026.
- Choosing a Medigap Policy (March 2026), Centers for Medicare & Medicaid Services. Checked September 29, 2026.
- Welcome to Medicare preventive visit, Medicare.gov. Checked September 29, 2026.
General information about the federal Medicare program, not advice about your situation. Figures are for 2026 unless stated and change every year; last reviewed September 29, 2026. Quote My Policy is a private company. Not connected with or endorsed by the United States government or the federal Medicare program.
Quote My Policy does not sell Medicare plans on this site. For plan-specific help, contact Medicare at 1-800-MEDICARE (1-800-633-4227) (TTY 1-877-486-2048, 24 hours a day, 7 days a week) or your State Health Insurance Assistance Program.