Checklist for Enrolling in Medicare and Supplemental Coverage

2019 Medicare Enrollment — October 15th thru December 7th.

Whether you’re a healthy older adult or have chronic health concerns, Medicare and its supplemental insurance plan – Medigap – can help ensure your medical expenses are limited and predictable, contributing to your overall financial health as you age.

Anyone who is a U.S. citizen or legal resident and is turning age 65 is entitled to an initial enrollment period that lasts seven months — beginning three months before your 65th birthday, including the month you turn 65, and ending thee months after you turn 65.

During this time you can enroll in Medicare Part A and Part B online at or by calling 1-800-772-1213. Enrollment is just one step in the process of ensuring you have proper health coverage in place during your golden years.

Here are a few tips for navigating the enrollment process:

  • To enroll in Medicare Part A (hospital insurance), you will need your Social Security number, current health insurance coverage, and Medicaid number and start/end dates, if applicable.
  • To enroll in Medicare Part B (medical insurance), you will first need to evaluate whether you need it. There is a 10% penalty that is added to your monthly premiums for each year you could have enrolled in Part B, but did not.
    • If you are still working and covered by an employer’s “qualified” employer-sponsored healthcare plan, you may qualify for a special enrollment period.
    • If you are already receiving Social Security retirement benefits when you turn 65, you should be contacted by the Social Security Administration a few months prior to eligibility and will automatically be enrolled in Medicare Part A and B.
  • After enrolling in Medicare, you can pick a prescription drug plan (Medicare Part D) during the seven-month period. You should consider what plan best covers the medications you use and understand how co-insurance and co-payments work with the plan you are considering.

The Medicare Supplemental Insurance Plan, Medigap, is a health policy sold by private insurers to fill any gaps in Medicare coverage. These plans help pay some of the health care costs that Medicare doesn’t cover, but do not always cover prescription drugs or dental procedures. Depending on your health-related issues, consider buying a plan within six months of enrolling in Medicare Part B if you need supplemental coverage.


Learn more about enrolling for Medicare coverage by downloading our comprehensive checklist.


PLEASE NOTE: JNBA is neither an agent of The Centers for Medicare & Medicaid Services, nor an insurance agent. All claiming strategies and benefits must be verified and accepted by The Centers for Medicare & Medicaid Services, no portion of the above should be construed as insurance advice. All insurance issues should be addressed with the insurance professional of your choosing.

Due to various factors, including changing market conditions and/or applicable laws, the content may no longer be reflective of current opinions or positions.  Moreover, you should not assume that any discussion or information contained in this blog serves as the receipt of, or as a substitute for, personalized investment advice from JNBA Financial Advisors, Inc.

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