Turning 65 comes with one of the biggest insurance decisions you will ever make, and the deadlines arrive whether you feel ready or not. Simple Retirement Benefits is based in Austin and works with clients by phone across Central Texas and in all 18 states where we are licensed, so you can get clear answers about your Medicare choices no matter where you live.
Schedule a Turning 65 ReviewWhat to Do Before Your 65th Birthday
A little preparation makes the transition to Medicare much smoother. In the months before you turn 65:
- Confirm your Medicare eligibility and whether you qualify for premium-free Part A.
- Mark your Initial Enrollment Period on the calendar. It begins three months before your birth month, includes your birth month, and ends three months after it.
- Decide whether you will keep working and keep employer coverage, or move fully to Medicare.
- List your doctors, prescriptions, and expected medical needs so any plan you consider can be checked against them.
- If you already receive Social Security benefits, watch the mail. Enrollment in Parts A and B is usually automatic, and your Medicare card normally arrives a few weeks before your birthday.
Your Coverage Choices: Parts A, B, C, D and Medigap
Original Medicare has two parts. Part A covers hospital stays, skilled nursing care, and hospice. Part B covers doctor visits, outpatient care, and preventive services. Most people take both at 65.
From there, you have two main paths. You can add a Medicare Supplement (Medigap) plan to help pay the deductibles and coinsurance Original Medicare leaves behind, usually alongside a standalone Part D prescription drug plan. Or you can choose a Medicare Advantage (Part C) plan, which bundles your coverage into a single plan, often with drug coverage included. Each path has tradeoffs in cost, provider access, and flexibility, and the appropriate fit depends on your health, budget, and travel habits.
Enrollment Deadlines and Late Penalties
Your Initial Enrollment Period is a seven-month window built around your 65th birthday. Missing it can be expensive. The Part B late penalty adds 10 percent to your premium for each full 12-month period you went without Part B when you should have had it, and it lasts for as long as you have Part B. Part D has its own penalty that grows for every month you go without creditable drug coverage.
There are also annual windows for changing coverage later, and special enrollment periods for situations like losing employer coverage. Our Medicare enrollment guide explains each period and the dates that matter.
Still Working at 65? Employer Coverage and HSA Questions
If you or your spouse is still working and you have health coverage through an employer with 20 or more employees, you can usually delay Part B without a penalty and enroll later through a special enrollment period. If the employer has fewer than 20 employees, Medicare generally needs to be in place at 65, so check before you delay anything.
Health Savings Accounts add another wrinkle. Once you enroll in any part of Medicare, you can no longer contribute to an HSA, and Part A can apply retroactively for up to six months when you enroll after 65. If you plan to keep contributing past 65, the timing of your enrollment matters, so review it before you file anything.
If Your Spouse Is Under 65
Medicare is individual coverage, so your spouse cannot join your Medicare plan. If your spouse is under 65 and loses coverage when you leave an employer plan, they will need their own coverage, such as an ACA Marketplace plan or employer coverage, until their own Medicare eligibility begins. We help couples plan both timelines together so nobody ends up with a gap.
How Simple Retirement Benefits Can Help
We're an independent advisor brokerage, we compare plans from multiple carriers and walk you through your Part A and B decisions, Medigap and Medicare Advantage options, and drug coverage, all matched to your doctors, prescriptions, and budget. When you need a customized review before you turn 65, our team is here to guide you.