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Enrolling in Medicare was never supposed to be this confusing.Years ago, the process was simpler. And less confusing. So, what has changed? And what can you do to simplify the process? We’ll consider each of those questions in turn.  


There are six factors that have made the Medicare
decision more complex.


1. The Normal Retirement Age (NRA) for Social Security benefits and the eligibility age for Medicare used to be the same – 65. Enrolling in Social Security and Medicare went hand in hand. You only had to keep one date in mind. The date you reached 65. In 1983, however, Congress changed the law gradually increasing the NRA from 65 to 67. The eligibility age for Medicare remained 65. With this change, enrolling in Social Security and Medicare was no longer a “one and done” deal. If you wanted an unreduced Social Security benefit you held off enrolling until your NRA. Your NRA now comes after your Medicare eligibility. This means at 65 Medicare enrollment is not automatic. You may go online ( and enroll or go to your local Social Security office to enroll in Medicare. 


3. More of us are retiring after 65. Years ago, most people (including your parents and grandparents most likely) retired at 65. And why not? Social Security and Medicare kicked in at 65. So, did most company pensions. Many of us have now begun working beyond 65. This has created confusion about staying on the employer’s group health plan versus enrolling in Medicare. The worker’s spouse, if over 65, faces the same question. Stay in the spouse’s employer group health plan or move to Medicare. 


3. Many employers have ended retiree health care plans. But many plans still exist. Employer retiree plans combine with Medicare to provide coverage.  Should you enroll in your employer’s retiree health plan? 


4. Add into the mix COBRA coverage, Medicaid eligibility and Obamacare plan coverage. Don’t forget Medicare eligibility before 65 because of disability. Your current health coverage will impact your Medicare enrollment decision. 


5. The introduction of Medicare Part D (prescription drug coverage) over ten years ago has added another set of decisions. Finding the plan that best meets your prescription drug needs at an affordable price should be done annually during the Open Enrollment Period that runs from October 15 through December 7.


6. Finally, the rise in popularity of Medicare Advantage (MA) plans. These plans come with or without prescription drug coverage (MAPD plans). Approximately one-third of all Medicare beneficiaries opt for a MA or MAPD plan. These plans can offer significant benefits. The different features make it important to consider each plan available in your area carefully. Recent legislation has broadened the benefits a MA or MAPD may provide beneficiaries. It also made making changes to coverage more flexible with the addition of the Medicare Advantage Open Enrollment Period which will run annually from January 1 through March 31. The first such open enrollment period kicked off in 2019.  More options, more confusion!


If you make the wrong decision regarding when to enroll in Medicare, you may face late enrollment penalties (that can be imposed for the rest of your life). Your enrollment dates may also be restricted. This may leave you with no health insurance of any kind for a period!



As you’ve probably figured out by now there is not a “cookie cutter” approach. Individual circumstances matter. Here is what you can do to make the process simpler. 


First, begin thinking about your Medicare enrollment well before your Initial Enrollment Period (IEP). Your IEP lasts seven months. It begins three full months before the month in which you turn age 65. It includes the month you turn age 65. It continues for the three full months after the month you turn age 65. You can also delay enrollment until after your IEP but that must be done with care. Note there are special rules for those born on the first of the month. Their Medicare eligibility begins the month before their birth month. 


Second, at least six months before your IEP begins do a “Medicare enrollment inventory” answering the following questions.


  1. Have you already started taking Social Security benefits before 65 or plan to do so before your IEP?

  2. Will you continue working after 65? Will you have access to an employer-provided group health plan? Does the plan include prescription drug coverage?

  3. Will your spouse continue working after you turn 65? If his or her employer offers a group health plan are you eligible?

  4. When you retire, does your employer (or union) offer a retiree group health plan? Is your spouse eligible for coverage?

  5. Do you have any of the following types of health care coverage: COBRA or an individual or family health plan (e.g., such as an Obamacare plan). Did you become eligible for Medicare before age 65 due to a disability? Are you eligible for Medicaid? Medicaid is a health insurance program provided by the federal and state governments. It is open to an individual with income and assets below certain thresholds. 


In subsequent articles, we will review the impact of these individual circumstances on your Medicare enrollment decisions.  IIII


Jim is a CPA and financial planner. Jim’s practice focuses on helping his clients think about and plan for the costs of health care in retirement. He has written over 100 articles on health care costs in retirement and a book on Medicare for the American Institute of Certified Public Accountants (the AICPA). He is currently writing a book for the AICPA on the impact of chronic and terminal illness on retirement plans. He lives in Glen Ellyn with his wife, 3 children and 2 Beagles.

CPA and Financial Planner

James Sullivan , MS, CPA, PFS



Making the process simpler

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