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Turning 65? Your Medicare Enrollment Checklist

October 29, 2026 · By Sonia Pilar Burke, CA Lic. #4402154

Turning 65 comes with a lot of mail, calls, and decisions. Here’s a simple checklist to help you get Medicare right the first time.

1. Know your Initial Enrollment Period

Your Initial Enrollment Period (IEP) is a 7-month window: the 3 months before the month you turn 65, your birthday month, and the 3 months after. Enrolling early in this window helps your coverage start without a gap.

2. Find out if you’ll be enrolled automatically

If you already receive Social Security retirement benefits, you’ll usually be enrolled in Medicare Parts A and B automatically and receive your card in the mail. If not, you’ll sign up through Social Security, online at ssa.gov, by phone, or in person.

3. Decide about Part B if you’re still working

If you or your spouse are still working and have health coverage through a current employer, you may be able to delay Part B without a penalty. The rules depend on the size of the employer and the type of coverage, so check with your employer’s benefits office before deciding. When that coverage ends, you generally have a Special Enrollment Period to sign up.

4. Avoid late enrollment penalties

  • Part B penalty: Your premium can go up 10% for each full 12-month period you could have had Part B but didn’t, usually for as long as you have Medicare.
  • Part D penalty: If you go 63 days or more without creditable drug coverage after you’re first eligible, a penalty is added to your drug plan premium, usually permanently.

5. Choose how you’ll get your coverage

Most people choose one of two paths:

  • Original Medicare (Parts A and B), usually with a stand-alone Part D drug plan and often a Medicare Supplement (Medigap) policy
  • Medicare Advantage (Part C), which bundles Parts A and B and usually Part D into one plan

Your first chance to buy a Medigap policy without health questions is generally during your 6-month Medigap Open Enrollment Period, which starts when you’re 65 or older and enrolled in Part B.

6. Gather your information

  • Your doctors and the hospitals you prefer
  • Your prescriptions, with dosages
  • Your preferred pharmacy
  • Any current coverage, such as employer, retiree, or Medi-Cal
Turning 65 soon? I’ll walk you through each step, at no cost to you, so you can enroll on time and avoid penalties.

Book a Complimentary Call   Call or Text (818) 213-0732

This article is for general educational purposes and is not a recommendation of any specific plan. Plan availability, benefits, and costs vary by plan and county and may change each year. For complete information, contact Medicare.gov or 1-800-MEDICARE.

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