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How Will Delaying Medicare At 65 Affect When I Can Sign Up In The Future Living In WNY?

By Andrew L Hibbard 
@WNYMrMedicare

Originally Posted: 24 JULY 2023
Updated & Revised:


For any and all Baby Boomers born in 1958 or later, who are willing working past 65, it is more important than ever to know exactly what to do with Medicare later in life, if you make the informed decision to wait, and delaying your benefits until after 65.

Now, this article is not going to address how to make that informed decision about should you, or shouldn’t you, sign up for Medicare at 65 if you’ll keep working, as I have addressed that question, and many others like it, in previous articles: 



The contents of this article will assume you’ve definitely decided on delaying your Medicare at 65, and now you smartly have new concerns and considerations around when you can sign up in future, sometime after 65.

So, let’s begin…

Unlike your gracious 7-month Medicare Initial Enrollment Period, or “IEP,” offered to you when signing up at 65, your post-65 enrollment period is a compressed and consolidated window of just 60-days prior to the date you need your Medicare benefits to begin.

Here’s an easy-to-understand example to explain…

Bill and Betty are married. Live in Clarence. And are two (2) years apart. Bill is turning 65 and Betty only 63.

Betty is a dependent spouse on Bill’s health insurance plan from his Employer, and they felt confused and clueless about what to do about Bill’s Medicare, and as important and impactful, how that would affect Betty.

After meeting with me, Bill and Betty shared that Bill wanted to keep working until about 67 to build back his 401k that has lost so much money over the past few years.

We worked together side-by-side to crunch the numbers, and I was able to put together a personalized “myMedicare SmartPath” planning workbook together, which revealed if Bill would keep working for the income, and went on Medicare at 65 for his health insurance, he could save thousands of out-of-pocket costs versus keeping his high-deductible health insurance plan from work.

But…(and a really critical and crucial but)…

Betty would be without health insurance, and have to shop the New York State exchange, and have to pay as much, or more, to insure herself with worse coverage.

Not a financially favorable situation for their family.

So, after reviewing and revising multiple options and outcomes, it was recommended the Bill keep his health insurance from work for both he and Betty.

Now, a new question needed an answer…

…and one many don’t think or know to ask… 
How Would Delaying Medicare At 65 Affect When Bill Can Sign Up In The Future?

For Bill and Betty, we plotted out and planned Bill working until December of 2025, and retire at the same time Betty would be turning 65 in January of 2026.

Both Bill and Betty would need Medicare to begin for January 01, 2026.

Keeping in mind the 60-Day Medicare enrollment window for Bill signing up after 65, we would need to fill out and file his Medicare application forms during the two (2) month period before needing Medicare to start --- which would be the months of November and December, since he needs Medicare to begin January 1st.

Once their Medicare application forms and filed, he will be assessed a late enrollment penalty based on the number of months which have passed from when he turned 65 (and was first eligible for Medicare) and the first day he will activate their coverage on January 1st.

He will be given the chance to disagree with this late enrollment penalty assessment and file a grievance with supporting documentation to prove he had “credible coverage” from active employment, at an employer with 20 or more employees.

Often, the option to submit supporting documents is close to, or after, when you request your Medicare to become effective so you will be retroactively refunded paying the late enrollment penalty when you really shouldn’t have paid it in the first place.

Procrastination is ill advised.

Proactive planning can lessen and lower the potential for problems.

The Federal Government has found new ways to be less effective and take longer to get their job done, so you must be prompt and purposeful in the coordination of your coverage to ensure no lapse, no gaps, and certainly avoiding at all costs having to pay for costly COBRA coverage to bridge the gap because things weren’t done right on time.

The loss of your Employer Group Health Plan (EGHP) along with signing up and starting your Medicare coverage will take an extensive and exhaustive effort to have your old coverage end and your new coverage begin as you wish, want and expect.

In many cases, mistakes or mishaps made with Medicare cannot be undone.

It is very difficult to get a “do over” with the government.

So, if you, like Bill, will choose to delay Medicare at 65, and you now need to sign up later in life, it is imperative and important you either have the knowledge and know-how to complete these requirements or you rely on someone or somewhere who can do-it-for-you and make sure your move to Medicare is smooth and seamless. 


Ok, there’s a lot to deal with, right? I get it.

And as an active adult in WNY, who’s always on the run, you need a smart solution to cut through all the clutter. 

If you want some light shed on your situation, your hand held the whole way, and making your move to Medicare simpler, easier, seemingly stress-free and almost effortless, I can do just that. Here's how...

NEARING AGE 65 AND AREN'T SURE WHERE TO START?

**If you are TURNING 65 IN 6-12 MONTHS, my #1 Amazon best-selling guidebook, "Starting Medicare Smartly" will give you a great overview of everything you need to know, before you need to know it. Instead of buying on Amazon for $12.99, let me send you a completely free, complimentary copy, all at my expense. Here’s the website to go to: https://www.startingmedicaresmartly.com

**If you are TURNING 65 IN 4-6 MONTHS, you should be getting ready to enroll and your paperwork prepared to either sign up at 65, or suspend --- you can't do nothing. If you don't have the time or desire to deal with doing any of the dirty work with Medicare yourself, OR, you feel frustrated, confused and kind of clueless about figuring out the fine print with Medicare, you can rely on my free Medicare SmartStart Program and let me take away all your stress of trying to tackle anything on your own. It's how I help people just like you. Weekly availability is limited to the first 10 folks, and maximum 40 per month. Don't delay. Learn more about my nationally recognized program, and how you can put it to work for you --- for free --- by going to https://www.medicaresmartstartwny.com

**If you are TURNING 65 IN 1-4 MONTHS, you are cutting it close to your Medicare late penalty period. If you have NOT yet filled out and filed your Medicare forms, you are behind and against the clock. It is URGENT we get together as soon as possible so I can do all I can to help you avoid paying a costly late penalty for life --- before it's too late! You can immediately schedule your emergency Medicare SmartStart Strategy Session with me at by clicking HERE (They go fast, so I hope there are still any available?)


HAVE MORE MEDICARE QUESTIONS?

Read the most common questions folks in WNY ask when they aren’t sure how to get started with Medicare. Feel free to browse the complete Medicare SmartStart Answers article archive at https://www.wnymedicare.org/smartstart_answers


ABOUT THE AUTHOR

Andrew L Hibbard is a prominent name when mentioning Medicare in WNY, but one you may have never heard of. Working behind-the-scenes, he is a best-selling author, expert advisor and successful agency owner. Focused on educating first, Andrew prides himself on being considered “the only advocate in WNY fighting for better and more reliable Medicare resources, free from insurance company conflict of interests.”

To take away the stress of trying to tackle Medicare alone and feeling forced to figure it all out by yourself --- Andrew created the WNY Medicare SmartStart Program; a free, step-by-step plan, that holds you by the hand to sign up and start Medicare smartly. (More than 850+ people have gone through the program and call it “the lazy way to get Medicare done for you without costing you a dime”).

**SPECIAL FREE GIFT** If you want to see how hundreds of WNY'ers each year are doing things different with Medicare, and getting it all done in record time, you can request a special "Medicare SmartStarter Info Kit” at no-cost to you, Andrew will give it to you as his free gift. It will prove, without a doubt, why his Medicare SmartStart Program is widely considered the most popular and preferred way to sign up and get started with Medicare in WNY, Guaranteed! You can request yours at https://www.medicaresmartstartwny.com/info right now and everything will be rushed to you right away. It's that easy!

You Can Feel Confident Knowing What To Do With Medicare.

I Can Take Away The Stress Of Trying To Tackle It On Your Own.

Figuring out all the fine print with Medicare doesn't need to feel stressful. You don't have to spend your scarce free time at home, alone, in isolation, relying on your own assumptions and hit-or-miss guesses, attempting to do-it-yourself.

Confidently knowing exactly what to do (and when) with Medicare is the key to avoiding future fines and fees and only my Medicare SmartStart Program will show you how.

If you don't have the time or the desire to deal with Medicare directly, and want a BETTER, SMARTER, time-saving solution to short-cut hours of your own trial and error so you know --- without question --- you aren't messing anything up making a mistake...

Let me put my proven Medicare SmartStart Program to work for you. 

Click the link below to take the next step and schedule a complimentary Medicare SmartStart Strategy Session with me --- it's that easy!

You Can Feel Confident Knowing What To Do With Medicare.

I Can Take Away The Stress Of Trying To Tackle It On Your Own.

Figuring out all the fine print with Medicare doesn't need to feel stressful. You don't have to spend your scarce free time at home, alone, in isolation, relying on your own assumptions and hit-or-miss guesses, attempting to do-it-yourself.

Confidently knowing exactly what to do (and when) with Medicare is the key to avoiding future fines and fees and only my Medicare SmartStart Program will show you how.

If you don't have the time or the desire to deal with Medicare directly, and want a BETTER, SMARTER, time-saving solution to short-cut hours of your own trial and error so you know --- without question --- you aren't messing anything up making a mistake...

Let me put my proven Medicare SmartStart Program to work for you. 

Click the link below to take the next step and schedule a complimentary Medicare SmartStart Strategy Session with me --- it's that easy!

Get Started For FREE!

medicare help sign up for Medicare Part B Erie county
Who Is Andrew Hibbard?
Since 2015, Andrew has helped over 850+ Western New Yorkers through his nationally recognized Medicare SmartStart Program, taking away all the stress from folks trying to tackle Medicare on their own. His impressive record of success has been gotten Andrew featured in Forever Young Magazine and the BEE Group Newspapers, exclusive interviews on WECK Radio's Senior Matter's Program, and author an #1 Amazon best-selling guidebook on the subject, "Starting Medicare Smartly," revealing how the rules specifically and significantly differ for NY residents versus other states.
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