Three months before
For most people this is when Initial Enrollment opens. Enrolling in these months is what lets Part A and Part B start on the first day of your birthday month. If your birthday is the 1st, those parts can start the month before. Confirm the date with Social Security. If you or a spouse is still working, do not decide to wait from this calendar. The 7-month window has the rule. Still working at 65? is the employer question.
Your birthday month
The window is still open. If you first enroll in this month, coverage usually starts the first day of the next month, not on your birthday. The eligibility date tool estimates the dates you type. It is not a determination from Social Security.
Three months after
The window closes at the end of the third month after your birthday month. Enrolling in these months usually means coverage starts the month after you sign up, so there can be a gap. After the window closes, a late penalty or the General Enrollment Period can apply unless another rule does. Late enrollment penalties explains the surcharge. It is not a bill.
This calendar is not October
Annual Enrollment is October 15–December 7. The dates and what you can change are on the 2027 Annual Enrollment page. If you are turning 65, use this calendar, not that window. Every enrollment window is the map of the other dates.