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There are multiple enrollment timelines and deadlines for Medicare, and you should understand the rules for each. Not understanding them can lead to missing a coverage window and even to financial penalties.

To enroll into Medicare, you can do so online by clicking here:

Or, if you are enrolling into Part B after leaving group coverage, you will need the application forms, available here:

For most people, enrollment into Medicare Part A (hospitalization) is automatic, and free. This is almost always the first step, and you will get a red, white, and blue card in the mail (if you haven’t already), prior to your 65th birthday. However, the remaining enrollment deadlines are somewhat tricky…

You will need Part B right away if you do not have retirement benefits through a former employer and are currently not on group coverage. You will not have outpatient coverage if you do not enroll, meaning no coverage at the doctor’s office, lab tests, day procedures, bloodwork, imaging, etc.

Enrollment Window: 7 months: The three months prior to your 65th birth month, that actual month, and the following three months. If your birthday falls on the 1st of the month, this timetable moves up 1 month.

Penalty for late enrollment: If you do not enroll into Part B at this time, then you will not be able to enroll until the following year from Jan 1 – March 31, and it won’t be effective until July 1. You will be penalized 10% for each full year you don’t have Part B, triggered when you finally enroll. You will not be able to enroll in a Medicare Supplement or Medicare Health Plan without Part B.

If you are drawing Social Security, they will simply deduct it from your monthly payment. If not, they will bill you, or you can sign up for Medicare Easy Pay.

You may need Part B if you are covered under group coverage and your employer has 20 or less employees, but you should always check with your former company's human resources department to be sure.

You may NOT need Part B if your current work will allow you to keep your coverage as primary after you turn 65 (Employers with over 20 employees). If this is the case, now you can simply compare it to the price of getting Part B, a supplement, and a drug plan. Once you finally leave the plan, you will have a Special Election Period of 8 months in which to get Part B and avoid any late penalties, but you only have 2 months from the time your benefits end to get a Prescription plan or a Medicare Health Plan. Choosing a health plan or medicare supplement will require that you are enrolled in Part B so please do so as soon as possible.

“So they sent me my Medicare card and it has both a Part A and Part B effective date on it, but I don’t need Part B yet.” This can happen if you are already drawing Social Security. Simply follow the instructions that came with your card and send back the card in the mail. If you enrolled through Social Security, you will have to contact them:

Prescription Drug Plans (PDP) or Medicare Advantage Plan enrollment:

Open Enrollment: 7 months-The three months prior to your 65th birth month, that actual month, and the following three months. If your birthday falls on the 1st of the month, this timetable moves up 1 month.

Special Election Period: such as leaving a group plan: 2 months from the time your benefits end for Prescription only coverage (which is what you would do if you were buying a Medicare Supplement), and 8 months from the time your benefits end if you are enrolling into a Medicare Advantage plan.

Annual Election Period (Oct 15 – Dec 7th): There are several other instances triggering a Special Enrollment Period, but if you are outside of these, then you can generally only enroll or change a plan during the Annual Election Period.

Penalty for not having a Prescription Plan: If you miss an enrollment deadline, and get a plan later, you will pay the normal premium, plus a permanent additional 1% per month of the average Drug Plan monthly premium for each month you weren’t enrolled.

Medicare Supplement Open Enrollment: You are considered eligible for Medicare Supplement Open Enrollment if your supplement will become active less than 6 months after your Part B effective date. You will not be asked any health questions on your application.

Medicare Supplement Guaranteed Issue. If you are working after age 65, and have already taken Part B, then terminate that coverage (most states even allow for voluntary termination), you can get a Medicare Supplement Plan F, A, or High Deductible Plan F without health questions for 63 days from the time the group coverage ends.