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
Turning 65…Medicare Marketing Is Overwhelming! America, it has finally happened because I, Toni King, who has been writing the Toni Says® Medicare column is turning 65 in May. I am now experiencing, excessive marketing and confusion regarding finding a Medicare plan...
Does Your Medicare Card Automatically Arrive in the Mail When Turning 65? Hello Toni: I turned 65 in December and have not received my Medicare card. I am working full- time with company benefits and not taking my social security check. A co-worker said I should have...
Is an MSA Like an Employer HSA Plan? Morning Toni: Never have I seen this question asked in your column. I am leaving employer’s insurance and have an HSA that has a $5000 deductible before the group health plan will begin to pay. I would like to know if there is a...
2020 Medicare Part D Changes…Released! Reader Alert: Effective October 1st, the new Medicare.gov website was released…. Toni: Last year, the 2019 Medicare and You handbook did not include the 2019 Part D deductibles and “Donut Hole” costs, and I got in the “famous”...
Under 65 What Should I Do During Medicare Annual Period (aka Open Enrollment)? Reader Alert: Effective October 1st, the new Medicare.gov Medicare plan finder was released. Navigating this site is not easy. Please take your time when searching a new Medicare Part D...
Toni Says® Tips for Medicare Open Enrollment Toni: I just received a phone call saying there is a federal law that I change my Medicare during Medicare’s Open Enrollment? The Toni Says® office helped us with our Medicare decision in January when my husband retired...
Medicare Annual Enrollment! What Do I Do? Dear Toni, This is my first Medicare Annual Enrollment and I don't know anything about this process? Which program is good, and which one is not? I do have some health problems and am concerned I am making the correct choice....
Questions About Transitioning Into Medicare... Hello Toni: You have been referred to me as a resource that can answer questions I have about Medicare. I am turning 65 this December and have not discovered what I need to do to begin Medicare since I am still working?...
America…. Enroll in Medicare Part B at the Right Time! Hello, Toni: My husband, John retired several years ago when he turned 65. He enrolled in Medicare Part A but declined Part B because I put him on my Blue Cross Blue Shield policy provided by my employer. Lately,...
Hello Toni, In May, my retiree benefits will be changing, and my husband and I will no longer be covered because we both will be 65. I am afraid that my husband and I will not be medically taken care of since we were forced to make this change and enroll in the...
