This can get confusing. If you are on a Medicare Supplement Plan, you can apply for a different plan year-round, 365 days a year. However, in most states, you can be rejected if you have preexisting health conditions and if you aren’t in your initial Medicare Enrollment period.
If you are on a Medicare Advantage (Part C) Plan and/or a Stand-Alone Medicare Part D drug plan, you can review and change or keep your existing plan between October 15 through December 7th of every year. Note: Special Enrollment Periods can apply for unique circumstances; for example, moving to a new county or state.
The new plan you select will always take effect on January 1st of the following year. Be careful, however. If you are on a Medicare Advantage Plan and enroll in a stand-alone Part D Drug plan, you will be dis-enrolled automatically from your Advantage Plan by Medicare itself.