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
Can Enrolling in COBRA Cause A Medicare Penalty? Dear Toni: I lost my job in September 2020 due to COVID layoffs in the oil industry and my wife and I are now enrolling in Medicare Part B since the company paid 18 months of COBRA is almost over…Now I am finding out...
Enrolling in Medicare Part B the Wrong Way is Stressful! Hello, Toni: My husband 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 I...
Turning 65 …Is Medicare Annual Enrollment Time for Me? Toni, I turn 65 in April and am overwhelmed by all the mail I am getting this year for Medicare Annual Enrollment. What do I do? The mail from companies says theirs is the best, but they all offer the same thing...
Questions About Turning 65, Still Working And Enrolling in Medicare Hello Toni: You were referred to me as a resource that can answer questions I have about enrolling in Medicare. I am turning 65 this January and have not discovered what I should do. Do I begin my...
Social Security Account Suspended…Need to Enroll Medicare Online!! Help Toni: I’m turning 65 in July and last week I tried to open a “My Social Security” account to enroll in Medicare online but my Social Security account is blocked. Two years ago, someone falsely...
Enrolling in Medicare Made Simple Hello Toni: My husband, David, has been laid off because of what is happening to the economy due to COVID-19. He is 68 and has never enrolled in Medicare, but I am turning 65 this June. We both are covered under his employer’s...
Stress Changing Medicare Plan Morning Toni: When I first got Medicare, I picked a Medicare supplement plan F. Two years ago, I was approached by a telemarking phone call. He talked me into plan K to save some money since I was in good health and could answer the...
Marketing During Medicare Annual Enrollment Is Stressful!! 3 Weeks until Thursday, October 15-Medicare Annual Enrollment- Toni: I just received a phone call saying there is a federal law that I change my Medicare during Medicare’s Annual Enrollment? The Toni Says®...
Toni: I am a confused Baby Boomer who needs to make my Medicare decision this October when I turn 65. I am currently on an individual health plan that has a terrible high deductible. I do not know where to start or what to do? Can you please simplify this ordeal? ...
Enroll in Medicare Past 65 and Losing Your Job During Current Hard-Economic Times Reader Alert: Tuesday March 17, 2020 all local Social Security offices nationwide were closed to in-person visits and have asked those who need assistance to call your local Social...
