Toni Says: Special Medicare Enrolling Circumstances



I have a different Medicare issue concerning how my husband and myself should enroll in Medicare when we retire in September and October.

I am turning 65 on August 23 and retire from my job effective September 1st when I will lose my employer benefits. I will not begin my Social Security until I turn 70. My husband Carl, who is 68 has never enrolled in Medicare Parts A and B or his Social Security benefits. He turns 69 October 8th and is retiring from his engineering firm effective October 1st when he will lose his employer benefits.

I am still a little unsure when I should apply for Medicare and when is the best time for my husband to have his Medicare begin since he is past 65. Thanks, Valerie from Pearland area


Your Medicare question is unique with two different enrollment times happening at the same time to the same family. Valerie, you will be turning 65 and will be in your “Medicare Initial Enrollment” period and your husband Carl who is past 65 will need to apply for a “Special Enrollment Period” which is a completely different process. 

Let me explain both types of Medicare enrollments:

Medicare Initial Enrollment Period: Begins 3 months before turning 65, the month one turns 65and 3 months after one turns 65.

Special Enrollment Period: Enroll after 65 when delaying Medicare Part B due to working full time with company benefits. This is an 8-month window of signing up for Medicare Part B without receiving a Part B penalty. 

Valerie, I would suggest that you enroll in your Medicare during the month you turn 65 which is August and your Medicare Part B will begin September 1st when you are retiring and losing your company benefits. You will be enrolling during your Medicare Effective Date Schedule.

At that time, you can apply for your Medicare Supplement with a September 1st effective date because you will also be in your Medicare Supplement/Medigap Open Enrollment Period. 

Below is the Medicare effective date schedule:

Enrolling anytime 3 months before turning 65, your Medicare begins the first day of the month you turn 65.

Enroll the month you turn 65 which is August, then Medicare will begin 1 month after you sign up. Enroll in August; and your Medicare will begin September 1st.

Enroll 1 month after you turn 65, your Medicare will begin 2 months after you sign up.

Enroll 2 months after you turn 65, your Medicare will begin 3 months after you sign up.

Enroll 3months after you turn 65, your Medicare will begin 3 months after you sign up.

Carl’s Medicare situation is different than Valerie’s because he is past 65 and retiring with “true” employer benefits. He needs Social Security form OMB #0938 (Request for Employment Information) from and have his HR department sign and date the form. In September, take the form in person to a local Social Security office to apply for Medicare Parts A and B.

Carl should advise the Social Security agent that he is losing his company benefits and needs his Medicare Parts A and B to begin October 1. He is in his Medigap open enrollment time and does not have to answer health questions.

For questions regarding the maze of Medicare, call the Toni Says® Medicare hotline at 832-519-8664.

February 2020 Confused about Medicare Workshop:

West Houston/Katy-Thursday, February 27th Spring Creek BBQ-Katy 6:00 – 8:00PM at Spring Creek BBQ-Katy- Banquet Room (dinner not provided) 21000 Katy Freeway, Katy, TX 77449 RSVP 832/519-8664 or visit and sign up via the Toni Says® website.

Toni King, author of the Medicare Survival Guide® is giving a $5 discount on the Medicare Survival Guide® Advanced book to the Toni Says Medicare column readers at 


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