Topics
Enrollment Periods
Initial Enrollment, Annual Enrollment, Open Enrollment and Special Enrollment Periods — which window applies to you, and what missing it costs.
Medicare does not let you change coverage whenever you like. Each kind of change has its own window: the seven months around your 65th birthday, the fall period every year, the first quarter for Advantage switches, and special windows triggered by events like leaving a job or moving.
Missing a window is one of the few Medicare mistakes that cannot be undone quickly — some carry a lifetime penalty, others lock you out for most of a year. The guides below map every period to the calendar, and the timeline tool marks yours.
Guides
All articles
Your Guide to Signing Up for Medicare: A Step-by-Step Approach
Learn how to sign up for Medicare Parts A and B, including when to enroll, what documents you need, and the step-by-step process via SSA.gov. Avoid late penalties.
Medicare Enrollment Periods: Don't Miss These Deadlines
Medicare has multiple enrollment windows. Missing them means penalties or coverage gaps. Learn every key deadline — IEP, AEP, OEP, and SEPs — explained clearly.
Decisions in this topic
- Employer coverage vs Medicare at 65Whether you can safely delay Medicare depends on your employer's size — and a few common assumptions about COBRA and HSAs cause lasting penalties.
- COBRA vs MedicareCOBRA keeps your old plan but does not protect your Medicare timing. Choosing it without a plan for Part B is one of the most expensive mistakes at 65.
- Annual Enrollment vs Medicare Advantage Open EnrollmentTwo enrollment windows, similar names, very different powers. Confusing them is how people get stuck a full year in a plan they meant to leave.
- Delaying Part B vs enrolling at 65Delaying Part B is either completely safe or quietly expensive, and one question separates the two: what kind of coverage are you delaying with?
