Enrolling in Medicare involves a handful of decisions and deadlines. This checklist walks you through what to gather, what to decide, and when to act — whether you're turning 65, retiring, or losing other coverage.
Before You Enroll: What to Gather
- Social Security number and proof of age (birth certificate or passport)
- Details of any current employer or union health coverage
- A list of your current medications and prescribed dosages
- A list of doctors, specialists, and hospitals you want to keep seeing
- Your Social Security or Railroad Retirement Board contact information
Step-by-Step Checklist
- Confirm your enrollment window. Most people qualify for a 7-month Initial Enrollment Period around their 65th birthday. See our enrollment periods guide for exceptions.
- Decide: Original Medicare or Medicare Advantage. Compare the two paths in our Medicare Advantage vs. Medigap comparison.
- Check if you need Part D (drug coverage). Going without it when you don't have other creditable coverage can trigger a late-enrollment penalty.
- Consider a Medigap policy if you choose Original Medicare and want to limit out-of-pocket costs.
- Enroll online, by phone, or in person through the Social Security Administration, or work with a licensed agent to compare plans in your area.
- Set a reminder for the Annual Enrollment Period (Oct 15 – Dec 7) to review your coverage every year.
Common Mistakes to Avoid
- Missing your Initial Enrollment Period and facing late penalties
- Assuming employer coverage automatically delays Medicare without confirming it qualifies
- Picking a plan without checking if your doctors and pharmacy are in-network
- Not reviewing your plan annually — costs and coverage can change every year
Frequently Asked Questions
When should I start this checklist?
Ideally 2–3 months before you turn 65, or as soon as you know your other coverage is ending.
Do I need an agent to enroll?
No, you can enroll directly through Social Security. However, a licensed independent agent can help you compare plans at no cost to you, since agents are paid by the insurance carriers.
What happens if I miss a deadline?
Depending on the situation, you may face a late-enrollment penalty that's added to your premium for as long as you have that coverage, or you may need to wait for the next enrollment window.