Medicare does not enroll you automatically unless you are already drawing Social Security. Most people have to act, and the window is fixed by your birthday. Here is the order of operations.
Six months out
- Confirm whether you will keep working and keep employer coverage past 65. If the employer has 20 or more employees, you can usually delay Part B without penalty. Fewer than 20, Medicare becomes primary and you should enroll.
- Find out whether your employer drug coverage is creditable. Human resources has a notice for this. It decides whether you can delay Part D.
- Make a list of your doctors and every prescription. Every plan comparison starts here.
Three months out: your window opens
Your Initial Enrollment Period is seven months long: the three months before your birthday month, the month itself, and the three months after. Enroll in the first three months and coverage starts the first of your birthday month. Enroll later and it starts the month after you sign up.
- Enroll in Part A and Part B at ssa.gov or by phone with Social Security.
- Decide the path: Original Medicare plus a Supplement and a Part D plan, or a Medicare Advantage plan.
- If you choose a Supplement, buy it in the six months after your Part B starts. During that window no carrier can ask health questions or charge more for a condition.
The month you turn 65
- Check that your Medicare card arrived and the Part B effective date is right.
- Enroll in your Advantage or Part D plan if you have not. Both require Part A and Part B to be active.
- If your birthday is on the first of the month, Medicare starts the month before. Plan around that date, not the birthday.
What the penalties actually are
- Part B: 10 percent added to the premium for every full 12 months you could have had Part B and did not. It lasts for as long as you have Medicare.
- Part D: 1 percent of the national base premium for every month without creditable drug coverage. Also permanent.
- Both are avoidable with timing. Neither is worth the gamble.
This guide is general information, not advice about a specific policy. Benefits, enrollment rules, and costs vary by state, carrier, and year. Confirm details for your situation with a licensed agent.



