• positive review  I am so thrilled to have this selection over with. The relief is beyond description. Joann listens and talks straight. And with me if I hear or feel something is off I will politely exit the conversation. My questions and feedback were truthfully answered and at no time did I get the feeling that I was being lead, pushed or a sales pitch was happening. It was great service. Thank you and thanks for listening.

    Pilan Sue Butts Avatar Pilan Sue Butts
    April 5, 2019
  • 5 star review  I found Joann on YouTube while researching supplemental insurance. Her videos are so easy to understand Medigap. I have been in contact via email and phone. I highly recommend watching her videos. Thank you Joann for making it easy to navigate this new chapter in my life.

    Tina Hiebert Avatar Tina Hiebert
    September 19, 2018
  • 5 star review  Best decision I made going through Remdigap. I must have watched 40-50 videos from several different carriers and they mostly seemed shady. One I spoke to Joanne and walked through options, receieved some quotes she took care of the rest with absolutely no pressure. Oh yeah, her videos are clear and concise.

    Joe Moynihan Avatar Joe Moynihan
    June 15, 2018
  • 5 star review  My husband and I have been researching Medigap and Part D plans for months. Once we thought we knew what we were doing, we would find out we didn’t! Lol! If we would have started here, with Joann and REMEDIGAP, it would have been painless! So thankful we found her! Watch the videos, ask ANY question, and rest assured you’ll get a competitive rate and ZERO pressure. We got a super fast response which was helpful with my work schedule. Joann is genuine, easy to talk to, has a great sense of humor! What a Godsend. Feels like good old-fashioned customer service to me. Grateful.

    Angele Navares Avatar Angele Navares
    April 30, 2018
  • 5 star review  I came across Remedigap by chance and after reading some of the reviews I knew I had to check them out. I am so glad I did!!! So glad I had to tell anyone who will listen…hence this review. I cannot thank Joann enough for answering my questions at the 11th hour! She has, hands down, provided me with the most consise straightforward answers to my questions. Without so much as a hint of pressure in one direction or a other, so refreshing…so very important in this day and age when healthcare coverage can be dauntingly confusing! I appreciate it so much!

    Elizabeth Tatge Avatar Elizabeth Tatge
    December 7, 2017
  • 5 star review  Phoned them “cold” – based on a local area on aging recommendation and several comments penned by Ms. Quinn on websites. Unlike ALL other agencts, only Joann refrained from asking for my commitment to by a plan through them. At the same time, Joann put some searches into play and has promised to phone me once more with additonal input. It was I who offered to write this testimonial. Withouit purchasing a policy, it is the only way I know to express my gratitude for her professional conduct and genuine concern. Thank you, Joann! PS: You can take the teacher out of the school, but you can’t take the schoolteacher away. Your videos are very clearly laid-out: like a carefully constructed lesson

    Karen P. Katz Avatar Karen P. Katz
    November 7, 2017
  • 5 star review  Highly recommend REMEDIGAP videos if you want to understand the Medicare/medigap maze. Joann was thorough in her responses to my questions and requests for rates. Undoubtedly, I will be contacting this company when it is time for me to purchase a medigap policy.

    Rick Graves Avatar Rick Graves
    September 27, 2017
  • 5 star review  Very professional and courteous service. I will have a long term relationship with this business!

    Jack Broome Avatar Jack Broome
    May 12, 2017
  • 5 star review  This was the best thing I could have done for my self every thing was explained to me so I could make the best choice for me.And when I need help later they will be there for me .

    Diane Langille-stone Avatar Diane Langille-stone
    September 18, 2016
  • 5 star review  I left my Medicare Advantage HMO for a Medigap Plan N — I’m so happy I made the change. Joann was there to help me every step of the way and make the process so easy. What could have been an overwhelming situation ended up being completely stress free, thanks to Joann.

    Lorraine Roche Avatar Lorraine Roche
    August 7, 2016

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When to sign up for Medicare Benefits

Enrolling in Medicare shouldn’t be stressful. However, there are many people who are completely overwhelmed by the process. And, one of the most common areas of concern is Medicare enrollment. It’s likely you’ll receive tons of mail about Medicare insurance. But, highly unlikely that any of it will inform you about when to sign up for Medicare benefits. 

When should you sign up for Medicare benefits?

Before I answer the question about when to sign up for Medicare benefits, let me assure you that enrolling in Medicare and understanding how it works doesn’t have to be complicated. I’ll show you how easy it is to figure out when to sign up for Medicare benefits. Keep in mind, there are three Medicare enrollment opportunities and it’s important to know which one(s) apply to you.

Signing up for Medicare when you’re first eligible

The most common time for people to sign up for Medicare is during the Initial Enrollment Period. It applies to anyone turning 65 years young. If you plan on retiring and you’re not going to have employer group health coverage, then this is the time to apply for Medicare Part A and Medicare Part B.

The Initial Enrollment Period lasts for 7 months. It begins 3 months before your birthday month. It includes your birthday month and the 3 months after.

If you sign up for Medicare during the 3 months before your 65th birthday month, in most cases, your coverage starts the first day of your birthday month.

However, if your birthday is the first day of the month, your coverage will start the first day of the prior month. So, if your birthday is May 1, your Medicare coverage will start on the 1st day of April.

But, if your birthday is anywhere between the 2nd through the last day of the month, your coverage will begin on the first day of that month. For example, a birthday on May 17 will result in an effective date of May 1.

Sign up for the best Medicare start date

When to sign up for Medicare benefits is extremely important when choosing a start date.

Now, if you enroll in Medicare during your birthday month or the 3 months after, your start date for Medicare coverage will be delayed.

So, if you want Medicare coverage to begin on the first day of your birthday month, then sign up for Medicare during the first 3 months of your Initial Enrollment Period.

When to sign up for Medicare benefits if you or your spouse will continue working

There’s a growing population who continue to work beyond retirement age. If you or your spouse will continue working and you keep the group employer health insurance, then you should consider delaying Medicare Part B.

Why delay enrolling in Part B?

Medicare Part B is medical insurance. In most cases, if you have group employer health insurance, you may not need to sign up for Part B.

Remember, you have to pay a premium when you sign up for Part B. That’s why many people under group employer health coverage delay Part B enrollment.

With that said, it’s highly recommended that you check with your employer Benefits Administrator to make sure their coverage is as good or better than Medicare.

It’s important to note that if you delay Part B, you can still sign up for Part A during your Initial Enrollment Period. Your employer group health coverage will work with Medicare, but there are rules about which insurance pays first.

You can find out who pays first and how Medicare coordinates with other coverage here: Medicare.gov | Which insurance pays first

You won’t be penalized for delaying Part B as long as you have continuous group employer health coverage. Once that ends, most people have an opportunity to sign up for Part B through the Special Enrollment Period.

The Special Enrollment period applies if…

…you or your spouse are still working and you don’t sign up for Part B (or A if you have to buy it) when you’re first eligible because you’re covered under a group health plan based on employment.

It allows you to sign up for Part B (or Part A if you have to buy it) anytime you’re still covered by employer group health coverage.  The Special Enrollment Period is an 8 month window that begins the month after the employment ends or the coverage ends, whichever happens first.

When to sign up for Medicare (1)

Signing up for Medicare when COBRA and Retiree Health Plan Ends

Unfortunately, COBRA and retiree health plans aren’t considered coverage based on current employment. So, you aren’t eligible for a Special Enrollment Period when that coverage ends.

So, keep that in mind and consider signing up for Medicare when you’re first eligible. Otherwise, you may be subject to an enrollment penalty.

Are there any other Medicare enrollment opportunities?

Sometimes people don’t sign up for Medicare during their Initial Enrollment Period. Which means the period of time they can sign up for Medicare becomes limited.

If you miss the Initial Enrollment Period and don’t qualify for the Special Enrollment Period, you can sign up for Medicare between January 1 and March 31. This period of time is known as the General Enrollment Period.

BUT BEWARE! Your coverage won’t start until July 1st of that year. It’s also possible that you’ll be penalized for signing up late.

When’s the best time to sign up for Medicare Benefits?

1) If you’re signing up for both Part A and Part B, apply for Medicare once your Initial Enrollment Period starts. This will allow you plenty of time to get your Medicare card before your 65th birthday month.

2) Most people apply for Part A during their Initial Enrollment Period if they plan on keeping group employer health coverage. Then they apply for Part B during the Special Enrollment Period. Ideally, it’s best to coordinate Medicare to start immediately after your group employer health coverage ends.

3) If you have Medicare because of a disability or receive Social Security benefits, you’re automatically enrolled in Part A and Part B.


Thank you for reading our article “When to Sign Up for Medicare Benefits?” . At REMEDIGAP, we strive to provide the tools you need to make informed decisions about your Medicare benefits. Our video page, blog articles and Facebook Page are full of valuable information to help you make important decisions about your Medicare coverage.

In addition, we’ve created a Medicare eCourse where you receive one email a day for a week. Each email covers important topics about Medicare and Medigap insurance. Most importantly the eCourse is designed to make Medicare less confusing. Sign up for the eCourse here ====> www.remedigap.com/ecourse

As you learn about Medicare, you may have many questions or none at all. Either way, we customize our approach based on your needs. Most importantly, our service is free to everyone!

In full transparency, independent insurance agents are compensated by insurance companies based on a policy commission schedule. It’s not standard procedure for an insurance agent to charge a consultation fee. If an insurance professional is asking you to pay for information, you should consider looking for a new agent.

So what are you waiting for? Just give us a call at 888-411-1329 or simply click on our quote form for free Medigap quotes. It’s an easy way to see just what we can do for you!

Additional Resources:

Medicare Enrollment – What you need to know.

Who Sells the Best Medigap Insurance?

7 Great Points about Medicare

Call (888) 411-1329 for your free consultation today!

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2 thoughts on “When to sign up for Medicare Benefits”

  1. Thank you!
    Joann, you have been more than helpful with all my questions and concerns regarding Medicare! You even took the time to personally speak to me when I was confused about enrollment periods, and beleive me when I tell you that it was very appreciated getting that advice.
    I have since that conversation, enrolled in part A and have received my card from health and human services. At this point it’s still up in the air about whether or not our group plan at my company is at the 20 or more employees since we are up and down with 20+ or 19- during the course of the last couple of years. So I’m awaiting a decision before I sign up for part B and if I do sign up I will definitely be in contact with Remedigap to find out my best options!
    Sincerely, Bill

    1. Bill, I appreciate you taking the time to write such kind words. It was a pleasure speaking with you about Medicare. I know you’ve been trying to get information about Part B for some time. It appears as if you’re the trail blazer for the employees going into Medicare after you. Hope you get an answer soon. Remember, I’m just a phone call or email away if you have any other questions.

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