When and how do I enroll in Medicare? You have seven months to enroll in Parts A, B, C & D: that period includes your birthday month, the three months prior to your birthday month and the three months after your birthday month. If you wait too long to enroll, then you will pay a monthly penalty for the rest of your life unless you have a valid reason to wait such as still being on your employer’s group plan (in most cases). You can enroll by phone or online. The website address is www.socialsecurity.gov/retirement.

When can I enroll in a Medicare Advantage Plan?

Your initial enrollment period for enrolling in a Medicare Advantage plan is the same as for enrolling in Part B. In order to enroll in a Medicare Advantage Plan you do need your Medicare Identification number which you normally receive within two weeks of enrolling into Medicare.

What if I want to continue working and stay with my group coverage?

If you want to keep working and stay on your employer’s group insurance program you can as long as what the employer provides is what Medicare deems “Creditable Coverage”. You should check with your employer to be sure that what you have is creditable coverage otherwise you will pay penalties for enrolling late into Part B down the road if you choose to keep working past turning age 65. You should also be sure that your drug coverage is also deemed creditable coverage otherwise you can end up paying a penalty for enrolling late into a Part D prescription drug plan down the road as well.

What if you do not like your current Medicare Advantage Plan and want to change?

You can change your Medicare Advantage plan once per year during open enrollment which occurs between October 15th and December 7th every year. As such, you really have a one year lock in as to whatever Medicare Advantage plan you choose.

What if I want to get out of Medicare Advantage and go back to Original Medicare?

You can opt out of Medicare Advantage once per year from January 1st through February 14th and go back to original Medicare.

Are there any other times that I can change Medicare Advantage Plans?

You can change Medicare Advantage plans under the following circumstances:

  • You move out of your plan’s service area; or
  • You have Medicaid; or
  • You live in an institution such as a nursing home or require extra help

When can you enroll in a Medicare Supplement Plan?

You have a guaranteed issue open enrollment which begins on your birthday and lasts for six months. After that, it is very difficult to get into a Medicare Supplement Plan so you need to decide initially if you want to go that route or not. Otherwise you will be limited in your options to just original Medicare or a Medicare Advantage Plan.