insights - all things legal

August 1, 2026

Making Sense of Medicare Enrollment

Enrollment deadlines and penalties, what Original Medicare doesn't cover, and choosing between a Medicare Supplement and Medicare Advantage

Turning 65 triggers one of the more consequential enrollment decisions most people will face, and Medicare's own vocabulary is often the first obstacle. This article explains what Medicare's Parts actually mean, when enrollment is required, the penalties for enrolling late, and how to weigh a Medicare Supplement (Medigap) plan against a Medicare Advantage plan.