Good Morning Ms. Toni: I am turning 65 in Dec and retiring because of my health. I had a triple bi-pass September 2013 and last week I talked with the office manager at my cardiologist’s office about me getting on Medicare and what I should do?...
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
My Wife Has TRS Medicare… Why Did I Lose My Retiree Benefits?
Toni: My wife is a retired teacher and we are both on her TRS-Care Plan and also on my retiree health insurance which I use for services at MD Anderson because I am undergoing cancer treatment. I have just found out that I’ve lost my retiree health...
How to Apply for Medicare Online…Avoiding Long Lines at Your Local Social Security Office!!
Hi Toni: I need your help about how to enroll in Medicare. I am turning 65 in November and when I called Social Security was I surprised when they told me to go online to sign up. They do not want me to go to the Social Security office and get a person from Social...
How to Navigate the Maze of Medicare When You Have Cancer!!
Hi Toni, I am turning 65, this June and have no idea what I should do because I have breast cancer? Currently I am on a COBRA policy from my old employer with all of my medical bills are now being met. The COBRA plan is costing me about $800 a month. But...
When Should My Husband Take His Social Security Check??
Toni: My husband has recently been laid off from his job and I am having a real stress moment. He has always provided the main income, but now my job is paying the monthly bills. My husband will not touch his 401K or cash in any CDs. Friends are advising him to go...
Why am I Charged Extra for My Part D Drug Plan?
Hello Toni: I have your Medicare Survival Guide, but I still am confused on an issue. My husband retired from an oil company with full benefits. We have both turned 65 this year and will now be going on Medicare. His company has automatically enrolled...
New to Medicare!! What do I do NOW??
Dear Toni, I will be turning 65 on September 2nd and absolutely don't know anything about Medicare, how to apply, when to apply where to apply? How to select to what and when?? Which Medicare plan is good and which one is not?? I own a small business (Just me and my...
Enrolling in Medicare Correctly… Absolutely Puzzles Me!!
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 February 23 of this year and will retire on March 10th when my wife turns 65. Company benefits will end March 31st and I would...
Clock’s Ticking… Medicare’s Open Enrollment Ends Saturday Dec. 7th!!
Hello Toni: "I was so glad I read your column on the Internet; I recently attended a Medicare Advantage meeting and was going to join with some reservations. After reading your article, I am thinking it may not be a good fit for me. My question is if I change to an...
Government’s Shutdown…How Do I Enroll in Medicare?
Hello Toni: With the government shut down, how do I enroll in Medicare? I am sure the Social Security office is a nightmare. Is there an easier way to do this without standing in line for hours? Neil from Sugar Land Good day Neil: With the government shutdown, many...
