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Most of us know we are eligible for Medicare at age 65, but do you know how and when to enroll? If you said no, rest assured, you are in the majority. We will cover most major scenarios along with some general information regarding the Medicare program.

When talking about retirement, remember that Social Security and Medicare are two completely separate programs. In 2020 full retirement age for those born in 1955 is 66 yrs. 2 months and increases by 2 months each year until those born in 1960 and later reach 67 as their full retirement age. You can begin receiving Social Security benefits at age 62 but it will be a reduced amount. You can also delay taking Social Security until age 70 and receive a larger monthly benefits check. Consult a Social Security adviser about what works best for you.  


Medicare eligibility. You are eligible for Medicare on the first day of your 65th birth month. For example, if your birthday is August 15th, your Medicare eligibility date will be August 1st. The exception to this rule is if your birthday falls on the 1st of the month. If your birthday falls on the 1st, your Medicare eligibility date is the 1st of the previous month. i.e. January 1st for a February 1st birthday.


So, if you are eligible for Medicare at age 65 and full Social Security benefits at age 66 or older, who reminds you at age 65 and tells you it’s time to enroll in Medicare so you don’t have a lifetime penalty? NOBODY... That’s right NOBODY! You’re on your own to figure it out.


Medicare will charge a late enrollment penalty if you don’t enroll in Medicare Part B when you are first eligible at age 65. Part B late enrollment penalties are calculated as an extra 10 percent for each full 12-month period when you should have had Part B but didn't. If you should have signed up at age 65, the penalty calculation is made using the time that elapsed between the end of your Initial Enrollment Period and the end of the General Enrollment Period (GEP) in which you finally sign up. This is a lifetime penalty. Usually, you don't pay a late enrollment penalty if you meet certain conditions such as creditable group insurance. If you want to enroll in Medicare Part B later and do not have documentation of creditable coverage, you will pay a late enrollment penalty.  Note: Under Medicare Part B, VA health care is NOT creditable coverage.


You enroll in Medicare Parts A and B through Social Security. If you have a Social Security account, you can enroll in Medicare online. You can also call Social Security and enroll over the phone. Sometimes you will have to make a phone appointment and that wait can be over two months in some cases. You can also go to your local Social Security office and apply in person.

You enroll in Part D through a private carrier. Your Initial Enrollment Period (IEP) begins at age 65 with your entitlement to Medicare Part A. You can get your prescription drug coverage through a stand-alone Part D plan or a Medicare Advantage plan that includes prescription drugs. Note: If you delay taking Part D because you have VA drug coverage, VA IS considered creditable coverage for Part D.


When should I enroll in Medicare?

Here are a few common scenarios.


Scenario 1. You took Social Security at age 64

Age 65 and currently enrolled in Social Security: You will be automatically enrolled in Medicare Part A and B and don’t need to sign up. Medicare will send you a "Welcome to Medicare" packet 3 months before you turn 65. Social Security will take your Part B premium out of your SS check the month before your effective date. You can refuse Medicare Part B by sending the card back and requesting only Medicare Part A. DO NOT DO THIS UNLESS YOU KNOW YOU HAVE OTHER CREDITABLE MEDICAL COVERAGE! See lifetime penalties above.


Scenario 2. Not currently employed or enrolled in Social Security

Age 65 not covered by a group employer plan and not enrolled in Social Security: You have a 7-month Initial Enrollment Period or IEP. You can enroll the 3 months before, the month of, and 3 months after your 65th birthday. If you enroll anytime in the 3 months before your effective date, your start date will be the first of your birth month. If you delay your enrollment past your initial election date, your coverage will generally begin the first of the following month. Remember, you can enroll online, over the phone, or in person. This is also the IEP for Medicare Part D through a private carrier. You can enroll in a Medicare Part D plan through or through a trusted local insurance advisor.


Scenario 3. Currently employed and covered by your or your spouse's employers group insurance.

Age 65 and currently covered by a group employers plan: You don’t have to sign up for Medicare and will not incur any penalties as long as you have documentation that you have creditable coverage. You will receive a letter in your insurance packet every year that tells you if your coverage meets the minimum standards. Most current group plans are considered creditable coverage. However, it is up to you to make sure your coverage is considered "creditable". The letters you receive will show this. Keep these documents in a Medicare file for proof when you do enroll in Medicare.

When you retire or want to drop your group insurance to enroll in Medicare, you will need your employer to fill out a form to give to Social Security as proof of creditable coverage so that you are not assessed the penalty. This employer letter that shows your last day of coverage will start your 8-month Special enrollment period (SEP) to sign up for Medicare Part B. Please note, COBRA and retiree benefits typically meet the minimum standards but do NOT give you a SEP to enroll in Medicare Part B. If you have not yet enrolled in Medicare Part B, you must use the General Enrollment Period (GEP) to enroll in Medicare Part B with your effective date being July 1st of that same year. The GEP runs from January 1st to March 31st of each year.

Enrollment in Medicare Part D with delayed Part B: If you have different Medicare Part A and Part B effective dates and have not enrolled in a Part D plan yet, you must enroll in a Part D plan within the 3 months prior to your Medicare Part B effective date. For example, your Medicare Part A effective date is January 1st, Medicare Part B effective date is July 1st, your Initial Enrollment Period (IEP) for Part D begins April 1st and ends June 31st. If you miss this enrollment period, you can enroll in a Part D plan during the Annual Election Period (AEP) that runs from Oct 15th through Dec 7th with coverage beginning January 1st. You may have to pay a late enrollment penalty if you have not had creditable coverage going back to when you first became eligible for Medicare. The late enrollment penalty is 1% per month times the national premium average. In 2020 the average premium is around $36 so not having coverage for 3 years would incur a penalty of 36% or roughly $12 per month. This is a LIFETIME penalty.


Enrollment in Medicare Part C (Medicare Advantage) follows the same rules as Medicare Part D but you MUST have Parts A and B to enroll in a Medicare Advantage plan. You must also live in the service area and cannot have End Stage Renal Disease (ESRD). ESRD rules are changing for January 1st, 2021 to allow those with ESRD the opportunity to enroll in a Medicare Advantage plan of their choice subject to service area availability. Most Medicare Advantage plans also include Part D coverage.


Enrollment in Medicare Supplements (Medigap) plans is open year-round as long as you have Medicare A&B. Medicare A&B have deductibles and cost sharing that you as the beneficiary are responsible for. If you are enrolled in Medicare A&B with no additional coverage, there is no maximum out of pocket limit you are liable for. Medicare Supplement plans are designed to pay these costs and fill in the coverage gaps. As of January 1st, 2020, Medicare Supplements can cover everything but the Part B deductible. Medicare Supplement policies are written by private carriers and you must apply for them separately from Medicare. These carriers can ask health questions (underwriting) and deny your coverage based upon your answers. Federal Medicare regulations prohibit carriers from asking these questions during the first 6 months you are 65 or older and enrolled in Medicare Part B. This is considered your Medicare Supplement Open enrollment period and can't be changed or repeated. Some states have different rules regarding underwriting and may not allow those questions.


Enrollment period cheat sheet:



Initial enrollment period for Medicare Part A, B, D


General Enrollment Period for Medicare Part B. Runs from January 1st to March 31st every year. Coverage is effective July 1st.


Initial coverage election period for Medicare Part C

SEP Part B   

Special Enrollment Period for Medicare Part B lasts for 8 months following loss of creditable Group Employment Insurance. Retiree or COBRA coverage not eligible for SEP.


Special Enrollment Period for Medicare Advantage plans. SEP’s are based upon personal individual circumstances such as low income or a change in residence.


Annual election period when you can change your Part D or Medicare Advantage plan. It runs from October 15th to Dec 7th every year with coverage beginning January 1st the next year.


Medicare Advantage Open Enrollment Period. You must be enrolled in a Medicare Advantage plan to take advantage of the MA-OEP. You have a one-time opportunity to change Medicare Advantage plans during the first 3 months of the year. You can also disenroll from your Medicare Advantage plan and enroll in original Medicare Parts A and B with or without a Medicare Part D plan. If you can pass underwriting, you can also enroll in a Supplement plan at this time.

Cheat Sheet
How to enroll
When to enroll
When w/SS
When IEP
When Group
When MA
When Part D
When Supplement
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