Dear Toni: I’m concerned about changing our Medicare Supplement plan that we have had for about 2 years, since we first got on Medicare. We received a pretty good rate increase in November of 2014 and I now have a new rate increase for this May 1st. I...
Enrolling in Medicare
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:
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Which enrollment period applies to you
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What to do if you’re still working (or covered through a spouse)
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How to avoid late penalties
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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
How to Enroll in Medicare Correctly and (Somewhat) Easily!!
With 10,000 Baby Boomers turning 65 everyday for the next 18 years, enrolling in Medicare can be very confusing! Most people think that when they turn 65, a magical switch is turned on and poof you are automatically on Medicare! Medicare changed the rules during the...
Turning 65 and Still Working…What Do I Do?
Toni: I am turning 65 in May 2015. I am currently employed and have medical insurance through my employer. I plan to work until 2016. Should I be doing anything relative to Medicare enrollment now? Thanks, Tom from Cypress, TX Morning Tom: Since 2015 has...
Waiting Until COBRA Ends to Enroll in Medicare’s Part B is DANGEROUS!!
Dear Toni: My husband lost his job June 2013 and we are now enrolling in Part B of Medicare because COBRA’s is almost over…Now I am finding out that there will be a penalty for us not enrolling when we should have. No one has ever told us when the time limit is and I...
Medicare Open Enrollment!! What Are My Medicare Options?
Dear Toni, This is my first Medicare open 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. If you can show me direction and help me, I...
Medicare Open Enrollment Begins Wednesday Oct 15– Are You Ready!!
Dear Toni: I’ve been told that I have to wait until Medicare’s Open Enrollment time to change my Medicare Advantage plan. I have just received a letter from my doctor saying they are no longer in the network for the Medicare Advantage plan I have and that I...
Navigating Enrolling in Medicare Rules What is my Effective date??
Toni: I have a very different Medicare problem concerning how to enroll than any problems, I’ve seen in your Medicare column. I turn 65 on Oct 10 of this year. I am on my husband’s group health plan and have already met my total out of pocket for this year. I would...
How to Enroll in Medicare at the Right Time!!
Hello Toni: I am turning 65 in December and have not started receiving my Social Security check. I am still working full time but do not have company benefits. I’m confused because I do not have Social Security and not sure how to get my Medicare. Do I call Medicare...
Wrong Medicare Decision Cost Me $5000 a Year!!
Hi Toni: I attended one of your seminars and now I need help with my Medicare/Social Security issue. I am 65 almost 66, “still working” and covered entirely by my company with an HSA insurance plan. I put about $5,000 per year into a tax sheltered account for medical...
Owe $64,300 To My Doctor and Rehab Center… Should Have Enrolled In Part B!!!
Toni, I am having a huge problem with my Medicare because I did not enroll in Part B at the correct time. I am 70 years old and 2 years ago was laid off from my job of 30+ years. A misguided friend advised me that I did not need to enroll in Part...
