Help on signing up for Medicare at 67

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So, I have a friend who has been working and is now 67. He has been offered a small buyout at work and is going to take it. He now needs to sign up for Medicare and is asking for my help.

First off, I have not done any research on this. It might be really easy to do...

But, he did not sign up for anything when he turned 65 as his HR dept said he had correct coverage. He called SS to ask and was told it could be 60 to 90 days before he could be covered. That sounds a bit strange to me but who knows for sure.

He worked for the city so he does have the correct coverage so he does not have to pay any kind of penalty.

Has anybody done this? What pitfalls do we have to worry about?
 
I did that last August, kind of. I retired on July 2nd, 2024. I was 67. My MegaCorp health insurance remained in effect until midnight on July 31, 2024. I had signed up for Medicare Part A on mySS when I turned 65 in June 2022. It was free, so why not be doubly covered, right? To be eligible for MegaCorp’s retiree health insurance I had to have Medicare Parts A and B, so about May, 2024 I signed up for Medicare Part B and my MegaCorp’s retiree health insurance to start on August 1, 2024. I did it online. I don’t recall if it was on mySS or my Medicare account, sorry. IIRC, my Part B and MegaCorp’s retiree health came online smoothly on August 1, 2025. Also, ditto for DW. We are on the Employee + Spouse rate.

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He can always use an independent insurance broker to help him sign up. It won’t cost him anything. I would try to steer him towards a Medicare Supplement plan over an Advantage plan though.
 
Yea... he is going to the supplement plans... he has heard enough problems with the advantage plans... he does have some chronic conditions where he has to have specialist and wants top care..
 
I recall being warned to sign up at 65, but I forget the consequences if I didn't. I had to anyway since my w*rk related insurance was going to be cancelled.
 
You don't have to sign up for Medicare at 65 years old if you are still covered by a "credible" medical plan with your employer. You should ask your employer's HR department if your company requires you to sign up for part A at 65 because this does vary by employer. You can sign up for free part A at 65 while you're working but if you do, you won't be eligible to contribute to an HSA nor will you be able to accept any free HSA contributions from your employer. You are not penalized if you wait to sign up for Medicare parts A and B past 65 as long as you've been covered under your employer's "credible" medical plan. The medical plans offered by most large companies are considered "credible" by Medicare rules. You sign up for Medicare on SSA.GOV/MEDICARE or through your local social security office. Also, you must stop contributing to your HSA account (your contributions and your employer's contributions) 6 months before you sign up for Medicare.
 
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I recall being warned to sign up at 65, but I forget the consequences if I didn't. I had to anyway since my w*rk related insurance was going to be cancelled.
I believe the consequences are if you don't sign up when you are first eligible, you will pay more when you do finally sign up.
 
You don't have to sign up for Medicare at 65 years old if you are still covered by a "credible" medical plan with your employer.

This. DH was always covered by my employer's plan from the day we married when he was 65. When I retired I was 61 and he was 76. We got creditable coverage letters from my 2 previous employers and that was enough for him to get Medicare B and D without any penalties.

Not sure why the OP's friend was told it would take so long to get coverage. We missed the first month for DH because the agent didn't get the enrollment in on time (fortunately no major claims in that period) but he had it the next month.
 
I believe the consequences are if you don't sign up when you are first eligible, you will pay more when you do finally sign up.
No, that is NOT correct. There is no penalty as long as you can prove (via a special form signed by your employer's HR department) that you had uninterrupted health insurance coverage since turning 65 AND the employer has/had 20 or more individuals on the payroll.
If you can't prove continuous coverage, then there is a 10% premium penalty for each full year for Part B and, a similar (though different) penalty for missed Part D. These penalties are FOR LIFE, and non-negotiable.
 
So talked to my friend again today... I cannot find the links of good brokers as I want him to talk to a broker or two... I know Boomer Benefits but who else is good?
 
So talked to my friend again today... I cannot find the links of good brokers as I want him to talk to a broker or two... I know Boomer Benefits but who else is good?
I have had good experience with medicareschool.com
 
So talked to my friend again today... I cannot find the links of good brokers as I want him to talk to a broker or two... I know Boomer Benefits but who else is good?
There's Chris Westfall at seniorsavingsnetwork.org
I should have gone with him, rather than the place I did, who so many seem to love since then. But not me! I've covered that here before.
 
Well, went over and signed him up for SS.... and clicked on the button to sign up for Medicare...

We called Medicare and was told it will take 5 to 10 days before he gets a Medicare number to be able to do anything....

Does anybody know if this also enrolls you in part A? There was nothing on the site asking about that.
 
It should have clearly stated that on the site. I think it automatically signs you up for part A, and the Medicare card should show that. Once you get the number you can see what the Medicare card looks like online at your Medicare.gov account.
 
Just read where they say if you start to receive SS you are automatically signed into A... we are starting his SS so that looks good..
 
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