Free Medicare Checklist

A plain-English, step-by-step checklist for signing up for Medicare and reviewing your coverage each year. Each step links to the official source on Medicare.gov or SSA.gov so you can check the details yourself.

Last reviewed: October 2026. 2027 premium and deductible amounts are set by CMS each fall. When they are published, check Medicare.gov’s costs page. We have deliberately left dollar amounts out of this checklist so it stays accurate.

Part 1: Turning 65 (or first becoming eligible)

  • ☐ Find your Initial Enrollment Period. It lasts 7 months: the 3 months before the month you turn 65, your birthday month, and the 3 months after. Signing up in the months before your birthday month helps you avoid a gap in coverage. Medicare.gov: when coverage starts
  • ☐ Check whether you’ll be enrolled automatically. If you already get Social Security or Railroad Retirement benefits before you turn 65, you are usually enrolled in Part A and Part B automatically and your card arrives in the mail. If not, you have to sign up yourself. Medicare.gov: how to sign up
  • ☐ Sign up through Social Security if needed. Apply online at SSA.gov, by phone at 1-800-772-1213, or at your local Social Security office. If you worked for a railroad, contact the Railroad Retirement Board.
  • ☐ If you’re still working, check your job-based coverage first. Whether you can delay Part B without a penalty depends on the coverage being from current employment (yours or your spouse’s) and on the employer’s size. Ask your employer’s benefits office how its plan works with Medicare. COBRA and retiree coverage do not count as current employment coverage. Medicare.gov: when you can sign up
  • ☐ Know your Special Enrollment Period. If you delayed Part B because of current job-based coverage, you usually have 8 months after that employment or coverage ends (whichever happens first) to sign up without a late penalty.
  • ☐ Understand the late penalties. The Part B penalty adds 10% to your premium for each full 12-month period you could have had Part B but didn’t, and it generally lasts as long as you have Part B. A separate Part D penalty applies if you go 63 days or more in a row without Part D or other creditable drug coverage. Medicare.gov: avoid late penalties
  • ☐ Have a Health Savings Account (HSA)? You can’t contribute to an HSA once your Medicare coverage starts, and premium-free Part A can be backdated up to 6 months when you sign up after 65. Talk to your HSA administrator or a tax professional before you enroll.

Part 2: Choose how you’ll get your coverage

  • ☐ Decide between Original Medicare and Medicare Advantage. Original Medicare (Parts A and B) lets you use any doctor or hospital that takes Medicare. You can add a Part D drug plan and a Medigap policy. Medicare Advantage (Part C) plans are offered by private companies and often use provider networks and prior authorization. Medicare.gov: your Medicare options
  • ☐ Make a list of your doctors, hospitals and prescriptions (drug name, dose and how often you take it). You’ll use it to compare plans.
  • ☐ Compare plans with the official Medicare Plan Finder. Enter your drugs and pharmacies to see estimated yearly costs, not just the premium. Medicare Plan Finder
  • ☐ Check each plan’s network, drug list (formulary) and rules such as prior authorization, referrals and preferred pharmacies.
  • ☐ If you want Medigap, know your best window. Your Medigap Open Enrollment Period is the 6 months that start the first month you have Part B and are 65 or older. During that time insurers generally can’t deny you or charge more because of your health. Medicare.gov: when you can buy Medigap
  • ☐ Don’t skip drug coverage unless you have other creditable coverage, so you don’t face the Part D late penalty later.

Part 3: See if you qualify for help with costs

  • ☐ Extra Help lowers Part D costs for people with limited income and resources. Apply through SSA.gov
  • ☐ Medicare Savings Programs (run by your state) can help pay Part B premiums and, for some people, deductibles and coinsurance. Medicare.gov: Medicare Savings Programs
  • ☐ Medicaid may also cover you if your income and resources are limited. Contact your state Medicaid office.

Part 4: After you enroll

  • ☐ Keep your Medicare card safe and give your number only to doctors, insurers and people you trust. Medicare won’t call you uninvited to ask for your Medicare number. Medicare.gov: report fraud
  • ☐ Book your “Welcome to Medicare” preventive visit within the first 12 months of Part B, then a yearly wellness visit after that. Medicare.gov: Welcome to Medicare visit
  • ☐ Create a Medicare.gov account to see your claims, coverage and preventive services. Medicare.gov account

Part 5: Every year (fall review)

  • ☐ Read your plan’s Annual Notice of Change, usually sent by the end of September, to see what is changing next year (premiums, drug list, network, copays).
  • ☐ Use Open Enrollment, October 15 – December 7. You can join, switch or drop a Medicare Advantage or Part D plan. Changes take effect January 1. Medicare.gov: when you can join or switch plans
  • ☐ Re-run your drugs through the Plan Finder every year. Plan formularies and pharmacy networks change.
  • ☐ Already in Medicare Advantage? The Medicare Advantage Open Enrollment Period (January 1 – March 31) lets you switch to another Medicare Advantage plan or go back to Original Medicare once.

Free, unbiased help

  • 1-800-MEDICARE (1-800-633-4227), available 24/7, or Medicare.gov.
  • Your State Health Insurance Assistance Program (SHIP) gives free one-on-one Medicare counseling: shiphelp.org.
  • Social Security: SSA.gov or 1-800-772-1213.

More guides: How to enroll in Medicare for the first time · Special Enrollment Periods · Medigap Plan G vs Plan N · Medicare Benefits Hub

Seniors Secrets offers research and education, not licensed insurance or medical advice. Please confirm plan details with Medicare.gov or a licensed advisor before enrolling. See our disclaimer.