To help you navigate these options and find the best plan for your needs, we’ve teamed up with Chapter to provide personalized, 1-1 guidance.


Preparing for Medicare enrollment can feel overwhelming, but an organized checklist will ensure that you cover all the necessary steps. From determining when you can enroll to understanding your coverage options, this checklist will guide you through each step to make the process smoother and more manageable.

Click here to download a printable checklist.

Medicare Enrollment Checklist

  1. Check Eligibility:
  2. Generally eligible if 65 or older and you or your spouse worked and paid Medicare taxes for at least 10 years.
  3. Determine When You Can Enroll:
  4. Initial Enrollment Period (IEP): 7-month window starting 3 months before your 65th birthday, including the month you turn 65, and ending 3 months after.
  5. General Enrollment Period: January 1 to March 31 annually.
  6. Special Enrollment Period: Available under specific circumstances, such as losing employer coverage.
  7. Explore Coverage Options:
  8. Original Medicare: Part A (Hospital Insurance) and Part B (Medical Insurance).
  9. Medicare Advantage (Part C): Alternative to Original Medicare through private insurers, often includes additional benefits.
  10. Medicare Part D: Covers prescription drugs, can be added to Original Medicare or included in some Medicare Advantage plans.
  11. Medigap: Supplemental insurance covering costs not included in Original Medicare (e.g., copayments, deductibles).
  12. Decide Between Original Medicare and Medicare Advantage:
  13. Compare benefits, costs, and provider networks to choose the best option for your healthcare needs.
  14. Review Current Insurance:
  15. Contact your benefits administrator if you have employer or union coverage to understand how it interacts with Medicare.
  16. Prepare Necessary Documents:
  17. Gather documents such as your Social Security card, proof of citizenship or residency, and current health insurance details.
  18. Sign Up for Medicare:
  19. Enroll through the Social Security website, by phone, or in person at a Social Security office.
  20. Review Your Plan Annually:
  21. Health and drug plans can change each year. Review your coverage during the Annual Election Period (October 15 to December 7) to ensure it still meets your needs.
  22. Check for Financial Assistance:
  23. Programs such as Medicaid, Medicare Savings Program, and Extra Help can assist with Medicare-related costs.

By following this checklist, you can ensure a smooth Medicare enrollment process. Take time to review your current insurance, prepare your documents, and explore all your coverage options to make informed decisions that will support your healthcare needs. Regularly reassess your plan to ensure it fits your evolving needs.


To help you navigate these options and find the best plan for your needs, we’ve teamed up with Chapter to provide personalized, 1-1 guidance.