Medicare Enrollment, Turning 65 and Retirement Guides
Choose the path that matches your situation. Enrollment at 65, working past 65, retirement and existing Medicare coverage do not follow one universal timeline.
Start with the Turning 65 guide if you are approaching Medicare for the first time. Use the working and retirement guides if employer coverage changes the timeline. Use the special-situation guides if you already have Medicare or need local planning.
Start Here
Enrollment and Effective Dates
Working, Retiring and Other Coverage
Special and Local Situations
What Determines Your Medicare Timeline?
Will enrollment be automatic?
Your Social Security or Railroad Retirement status can determine whether a card arrives automatically.
Read the automatic enrollment guide →What coverage do you have?
Current-employment group coverage is treated differently from COBRA, retiree or Marketplace coverage.
Compare coverage types →Who pays first?
Employer size and the reason for Medicare eligibility affect coordination.
Review the payer rules →Who else depends on the plan?
A spouse or dependent may need separate coverage when the employee moves to Medicare.
Plan coverage for a spouse →Information to Gather
- Your expected retirement and coverage-end dates.
- Whether coverage is based on current employment.
- The employer’s official Medicare coordination size.
- Your Social Security or Railroad Retirement status.
- Any HSA contributions by you or the employer.
- Doctors, facilities, prescriptions and pharmacies.
- The spouse or dependents who need replacement coverage.
Frequently Asked Questions
When should I begin preparing for Medicare?
Begin at least three months before the desired start date. Six months gives more time when employer coverage, an HSA, retirement or a spouse’s coverage is involved.
Does everyone automatically receive Medicare at 65?
No. Automatic enrollment generally depends on receiving qualifying Social Security or Railroad Retirement benefits before age 65.
Can I delay Medicare because I am still working?
Possibly, when you have qualifying group coverage based on current employment. Employer size and payer order must also be confirmed.
Does COBRA extend my Part B enrollment period?
No. COBRA does not extend the working-aged Part B Special Enrollment Period.
Can Marketplace coverage replace Medicare at 65?
Most people eligible for premium-free Part A should enroll in Medicare and generally lose eligibility for Marketplace financial assistance for their own coverage.
Do I need to stop HSA contributions?
Yes, for Medicare-covered months. Retroactive premium-free Part A can require contributions to stop months before an application.
Can Thompson Medicare Brokerage enroll me in Parts A and B?
No. Social Security or the Railroad Retirement Board handles Parts A and B. We help compare the private Medicare coverage choices that follow.
Sources and Enrollment Resources
Build the Enrollment Path Around Your Actual Coverage
Benjamin Thompson can help people in Missouri and Illinois compare the private Medicare options represented by Thompson Medicare Brokerage and organize the questions to take to Social Security, employers, the Marketplace or a tax professional.
Thompson Medicare Brokerage is not connected with or endorsed by the U.S. government or the federal Medicare program. This resource center provides general educational information. Official enrollment, effective-date, coordination and tax decisions depend on the individual situation.