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
NewMedicare Annual Enrollment Period: What You Can Change
Learn what you can and cannot change during Medicare's Annual Enrollment Period (October 15-December 7). Make informed plan decisions for next year.
Medicare Advantage Open Enrollment: Your January-March Choices
Understand the Medicare Advantage Open Enrollment Period (MA OEP) from January 1 to March 31. Learn who can use it, what changes you can make, and how it differs from other enrollment periods to choose the right plan.
Your One-Time Medigap Open Enrollment: Why This 6-Month Window Matters
Learn about the critical 6-month Medigap Open Enrollment Period. This one-time window allows you to buy a Medigap policy regardless of health, ensuring predictable medical costs.
Understanding Your Medicare Initial Enrollment Period (IEP)
Learn about your 7-month Medicare Initial Enrollment Period. Understand when it starts, what steps to take, and avoid late enrollment penalties.
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 EnrollmentThe Annual Enrollment Period runs October 15 to December 7; Medicare Advantage Open Enrollment runs January 1 to March 31. Here is what each one lets you change.
- 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?
Watch
1:38Medicare Advantage Open Enrollment Period: 1 change you can make
2:07Annual Enrollment Period: What Medicare Changes You Can Make
1:08Understanding Your Medigap Open Enrollment Period: A 6-Month Window Explained
1:06How to Sign Up for Medicare: SSA.gov Enrollment Walkthrough
1:28Enroll in Medicare: SSA.gov Steps & What You Need
1:09Your Initial Enrollment Period: When Does It Start?