Every Deadline is Here
Individual health insurance: December 15th is the last day to apply, if you want health insurance coverage to begin on January 1. January 15th is the last day to apply if you want health insurance to begin on February 1.
Medicare: December 7th is the last day to enroll in a Medicare Part D plan or Medicare Advantage plan. There is zero flexibility, unless you are entitled to a Special Enrollment Period. Note that December is irrelevant if your Medicare coverage begins January 1 – March 1.