Getting started with Medicare can be confusing, especially when you’re trying to figure out when to enroll, what it costs, and how employer coverage fits in.
This page pulls together our best articles that answer common Medicare enrollment questions, like:
Which enrollment period applies to you
What to do if you’re still working (or covered through a spouse)
How to avoid late penalties
What happens if you miss a deadline
Browse the articles below to find the guidance that matches your situation.
READ: What Is Medicare? 2026 Beginner’s Guide to Understanding Your Coverage Options
October 15 is coming…. Know your Medicare Open Enrollment Period options!! Dear Toni: I turned 65 in February and did not enroll in a Medicare Prescription Drug plan. I have been told that I must wait until October for Medicare’s enrollment time. I need help now...
Rules for enrolling in Medicare when self-employed are confusing! Dear Toni: I am self-employed with an individual health plan and confused about enrolling in Medicare when I turn 65 in July. I cannot find the answer to my situation in the Medicare & You handbook....
What is Medicare’s General Enrollment Period? Toni: I turned 65 in June, 2 years ago and did not enroll in Medicare because I do not have any health issues. A friend advised me to enroll in Medicare during Medicare’s Annual Enrollment Period. I received a letter...
Changes Available During Medicare’s AEP… Toni: In August, my husband and I enrolled in a Medicare Supplement, which has not paid a medical claim because we are in a Medicare Advantage plan. We could not leave the Advantage plan and return to Original Medicare...
Does Enrolling in a Medicare Supplement Cancel a Medicare Advantage Plan? Toni: Last year during Medicare’s Annual Enrollment, both my husband and I qualified for a Medicare Supplement Plan G over the phone from a telemarketing call. The supplement has never paid a...
New Medicare Turning-65 Enrolling Rule! Toni I have a quite different Medicare problem concerning how to enroll in Medicare than any enrollment problem that I have read in your Medicare column. I understand from an email a friend received from Medicare.gov that...
Know Your Medicare Annual Enrollment Options!! Dear Toni: I turned 65 in February and did not enroll in a Medicare Prescription Drug plan. I’ve been told that I must wait until October for Medicare’s Annual Enrollment time. I need help now because I have been...
Tips to Taking the Stress Out of Medicare Annual Enrollment Toni: Read in your column last week that there is only 3 weeks to the Medicare Annual Enrollment period. I’m really confused on what I need to do. I am receiving so much mail that I am stressed about...
Should I Enroll in Medicare When Turning 65? Hello Toni: I am turning 64 soon and have not started receiving my Social Security check. I am still working full time but do not have company benefits. I am confused because I do not have Social Security and not sure how...
Why Is My Medicare Premium an Extra $499? Toni: My husband, John and I need your guidance because I believe I have made a mistake enrolling in Medicare. Last year, John was laid off and lost his employer health insurance. I have enrolled in Medicare since I am...
