ENROLLMENT WINDOWS AND TIMING

Pay attention to your Medicare enrollment window. If you miss it, you might have to pay a penalty, pay more for coverage or have fewer choices.

  Initial
Enrollment—
When
Initial
Enrollment —
How
Late
Enrollment
Making
Changes
Part A Anytime from three months before your 65th birthday to three months after the month of your 65th birthday. Automatic, if you're already receiving Social Security benefits. Otherwise, enroll at your Social Security Office. There are no penalties for signing up late, unless you pay a monthly premium for Part A. Renews each year automatically.
Part B Same as Part A. Automatic, if you're receiving Social Security benefits when you turn 65 or otherwise become eligible for Medicare. If you're not receiving Social Security benefits, sign up at your Social Security office. You can also refuse coverage at this office. If you enroll after the initial enrollment period, premiums will be higher unless you qualify for an exception. Renews each year automatically.
Part C (Medicare Advantage) Anytime from three months before your 65th birthday to three months after the month of your 65th birthday. Enroll through a private insurance company. If you miss the enrollment window, you must wait to join a plan during the Annual Enrollment Period unless you qualify for an exception. The Annual Enrollment Period is October 15 to December 7 every year.
During the Annual Enrollment Period, you can change your plan, including adding or dropping Medicare Part D drug coverage. This is the only time of year you can do this, unless you qualify for an exception.
Medicare Part D (prescription drug coverage) Anytime from three months before your 65th birthday to three months after the month of your 65th birthday. Enroll through a private insurance company. If you miss the enrollment window, you must wait to join a plan during the Annual Enrollment Period unless you qualify for an exception. The Annual Enrollment Period is October 15 to December 7 every year.
During the Annual Enrollment Period, you can add, drop or change your Part D coverage. This is the only time of year you can do this, unless you qualify for an exception.
Medicare Supplement Insurance When you turn 65 and enroll in Medicare Part B, you have a guaranteed right to buy a Medicare Supplement policy for six months. You buy Medicare Supplement Insurance through a private insurance company. If you miss the enrollment window you can apply at any time. But you may pay a higher rate or be rejected if you have a history of health problems. You can add or drop at any time. If you change policies, it's best to wait until the new policy is effective before dropping the old policy.

Exceptions and special enrollment periods

There are some exceptions to dates and deadlines described above. In some cases you will have the right to change your coverage without waiting until the next Annual Enrollment Period.

For example, if you have a Medicare Advantage plan and you move out of your plan's service area, you can change your coverage without waiting for the next Annual Enrollment Period.

If your circumstances change, don't assume you must wait until the next Annual Enrollment Period. Call the Medicare Helpline at 1-800-MEDICARE (1-800-633-4227), 24 hours a day, 7 days a week (TTY users, call: 1-877-486-2048) and ask if your situation qualifies you to make changes outside of the timing rules.

https://aarphealthcare.com/content/aarphealthcare/home/understanding-health-products/ready-for-medicare/enrollment-windows.html