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Medicare Enrollment: How it Works

Oct 23, 2023 | Your Health

Navigating Medicare can be overwhelming. This insurance program is designed to help Americans in need, but many may not know if they are able to receive its benefits. Understanding eligibility and when to sign up can be confusing.

“Medicare is a federally-funded program,” explains Ben Rothering, a licensed insurance salesman who specializes in helping guide people through the Medicare process. “It’s health insurance for seniors, typically for people who are getting ready to turn 65. It can be available for people who are under the age of 65 if they qualify due to some sort of medical requirements. For example, if they have a disability that qualifies them or permanent kidney failure, that can also get them into Medicare earlier.”

Enrolling in Medicare

Previous generations had to wait in line at their nearest Social Security Administration office or endure phone calls to begin the Medicare enrollment process. For efficiency, visit and set up a Social Security account. Once your account is created, your enrollment will fall into one of three timelines: initial enrollment, special enrollment, or general enrollment.

Initial Enrollment

The initial enrollment period is designed for those about to turn 65. This window is seven months: three months before your birth month, your birth month itself, and three months following your birth month. For example, if your 65th birthday is in April, your initial enrollment window lasts from January 1 to July 31. If you plan to begin Medicare at age 65, enroll during this initial enrollment period.

Special Enrollment

Some individuals choose to continue working beyond age 65, and they may still have group coverage through their employer. Others over age 65 may have insurance coverage through a spouse. When their coverage is coming to an end, they can take advantage of the special enrollment period. For special enrollment, they must have a qualifying event (loss of insurance over age 65) to enroll in Medicare without a penalty for signing up outside of the initial enrollment window.

General Enrollment

For those over 65 who are not otherwise insured and missed the initial enrollment window, their opportunity is the general enrollment period. Between January 1 and March 31 every year, these individuals can apply for Medicare. If they miss this window, they can apply in July with penalty. “There’s a 10% penalty per year for every year that is delayed in picking up Medicare if you didn’t have any other health insurance that would be considered as credible coverage,” mentions Rothering.

Need Further Assistance?

Rothering, a former schoolteacher, is dedicated to helping people understand Medicare. “I know that Medicare can be very confusing for a lot of people. If I can help try to smooth out the process, that’s my goal. I don’t charge consulting fees or anything like that.” Rothering can be reached by cell at (608) 354-3869 or by email at

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