Enrolling in Medicare

medicare enrolment questions and answers on tonisays.com

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

Turn 65 April 30th Didn’t Enrolled in Medicare

Turn 65 April 30th Didn’t Enrolled in Medicare

Toni: My husband’s employer group health plan now has a $2500 deductible and the premium is over $600 for me.  The HR manager confided to Carl that Medicare may be a less expensive option for us since I turn 65 on April 30th and gave him a Toni Says® newspaper article...

Mom…Didn’t Enroll in Part D…Help!

Mom…Didn’t Enroll in Part D…Help!

Dear Toni: I have been told that Medicare does not cover drugs when you are in an emergency room?  My mother went in the hospital from the ER for 2 days and because it was considered “under observation, we are now fighting the hospital because they say her drugs were...

Myth or Fact…I’m Losing My Retiree Insurance

Myth or Fact…I’m Losing My Retiree Insurance

Hello Toni, I am a TRS retiree and you are aware that my TRS Aetna Retiree plan was cancelled.  I am concerned that my husband and I are not going to be taken care of medically since we are forced to change to the new TRS Medicare Advantage plan. I have heard from...

Times Running out… Medicare’s Open Enrollment Ends Dec. 7th!!

Times Running out… Medicare’s Open Enrollment Ends Dec. 7th!!

Hello Toni: I recently attended a Medicare Advantage meeting and was going to join with some reservations. After reading your article about the different Parts and Plans of Medicare, I am concerned that this Advantage plan may not be a good fit for me. My question is...

Can Enrolling in a Medicare Supplement Cancel a Medicare Advantage Plan?

Can Enrolling in a Medicare Supplement Cancel a Medicare Advantage Plan?

Toni:         Last year, both me and my husband purchased a Medicare Supplement Plan G. The supplement has never paid a dime! We are still having to use the same doctor and get referrals from our Medicare Advantage HMO that we were using in 2016.             Now the...

Steps To Do Your Own Medicare Part D Prescription Drug Planning

Steps To Do Your Own Medicare Part D Prescription Drug Planning

Toni: Last year’s Medicare Open Enrollment season, my husband, Steve and I changed from our Medicare Supplement Plan with a separate Part D plan to a Medicare Advantage PPO plan.  We were told that our doctors were in the plan and all of my husband’s diabetic meds...

Help!!! Doctor Not Accepting  Medicare Advantage Plan!!

Help!!! Doctor Not Accepting Medicare Advantage Plan!!

Toni:             Last year, I made a mistake and changed to a Medicare Advantage Plan because I understood from talking with my friends that this PPO plan was like a Medicare Supplement. Boy, was I wrong! I want out!! Most specialists and even the facility that does...

Texas Teacher Alert…Medicare Options TRS is NOT Disclosing!!

Texas Teacher Alert…Medicare Options TRS is NOT Disclosing!!

Toni: I am a retired Texas teacher and I am turning 65 this October. I am absolutely mortified by the TRS changes that I am hearing through the grapevine. My doctor is not accepting Humana Medicare Advantage and I am concerned about future health issues.  I have...

Little Secrets to Enrolling in Medicare Correctly!!

Little Secrets to Enrolling in Medicare Correctly!!

Hello Toni: I am turning 65 this September and have great retirement benefits from the company I worked for 20 plus years.  I have spoken with HR about what I need to do with enrolling in Medicare and they advised me not to enroll in Part B because I have...

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