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Jenkins Insurance & Retirement is a private insurance practice not affiliated with or endorsed by the U.S. government or the federal Medicare program.
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Free Printable Checklist

Turning 65 Medicare Checklist

Everything to handle before, during, and after your 65th birthday — on one page you can print, stick on the fridge, or hand to a family member.

Prints on a single page — great for sharing with a spouse or adult child helping you plan.

Jenkins Insurance & Retirement

Turning 65 Medicare Checklist

6 months before your birthday

  • Confirm you're eligible for premium-free Part A (you or your spouse worked ~10 years / 40 quarters)
  • List your current coverage: employer plan, COBRA, ACA plan, VA/TRICARE, or none
  • If you'll keep working past 65, ask HR whether your employer coverage is "creditable" and how it coordinates with Medicare
  • If you contribute to an HSA, plan to stop contributions before Medicare starts — enrolling can end HSA eligibility retroactively when you sign up for Social Security

3 months before (your enrollment window opens)

  • Your 7-month Initial Enrollment Period starts 3 months before your birthday month
  • Decide your path: Original Medicare (+ Medigap + Part D) or Medicare Advantage
  • Make a list of every doctor you want to keep — then verify they're in-network for any plan you consider
  • List every prescription with dosage, and check each plan's drug formulary
  • Compare total costs, not just premiums: deductibles, copays, and the plan's out-of-pocket maximum

Enrollment

  • Enroll at ssa.gov, by phone, or with free help from a licensed advisor
  • Coverage typically starts the 1st of your birthday month (a month early if you were born on the 1st)
  • If you're already receiving Social Security, you'll be enrolled in Parts A & B automatically — watch the mail for your card
  • Delaying Part B without creditable employer coverage adds a permanent late penalty — don't skip it by accident

After you enroll

  • Confirm your Medicare card arrived and your plan ID cards match what you chose
  • Set a yearly reminder for Annual Enrollment (Oct 15 – Dec 7) to re-check your plan
  • Tell your doctors and pharmacy about your new coverage
  • Keep records: enrollment confirmation numbers, plan documents, and agent contact info in one folder

This checklist is general education, not personalized advice. Enrollment timing rules have exceptions (disability, ESRD, working past 65, and more) — when in doubt, ask before you delay.

Jenkins Insurance & Retirement · (435) 538-3474 · jjenkins@crsgadvisors.com

Printed from jenkinsir.com — free Medicare & insurance guidance for Wyoming and Utah

Want someone to walk through it with you?

Jordan does this checklist with Wyoming and Utah families every week — a free call now can prevent a permanent penalty later.

(435) 538-3474