Transitioning to Medicare

By February 5, 2026Newsletter
American Continental Supplemental Insurance

Seniors often feel confused when they move from Group Insurance to Medicare, and conversations with friends or HR can make things even harder to sort out. These simple scenarios can help you understand your options more clearly.


Turning 65 while working for a large company (over 20 employees)

If your employer plan offers strong coverage, or your younger spouse still needs it, you can keep your Group Insurance, enroll in Medicare Part A, and delay Part B. You won’t pay Medicare premiums yet, and you can start Part B with a Supplement or Advantage plan whenever you’re ready.

Stop all HSA contributions, since Medicare doesn’t qualify as a high-deductible plan. Also confirm with HR that your group plan is creditable under Medicare rules.


Turning 65 while working for a small company (under 20 employees)

You must enroll in Medicare, because Medicare becomes primary. Your employer plan becomes secondary if you choose to keep it. Many seniors save money by dropping the group plan entirely, and I’m happy to help you compare both options.


Enrolling in Medicare at 65 and dropping your employer plan

This path works well if your group plan has high premiums or a high deductible. A Medicare Supplement or Advantage plan often lowers your costs and improves your coverage. Most people can drop their employer plan the month they turn 65.


Dropping your employer plan after Medicare is already active

Many seniors enroll in Medicare at 65 because they fear penalties, yet they keep their employer plan for years. When they retire, they discover they’ve carried double coverage. This situation can feel confusing, but we help seniors through it all the time and can guide you step-by-step.


Every senior’s transition to Medicare looks a little different. We consider it a privilege to help you make that move in the simplest and most affordable way possible.

If you’d like to talk through your Medicare questions, please give us a call at 800-750-2407. We’re always happy to help.

God Bless!