Turning 65
Your first Medicare enrollment, step by step
The decisions you make in this one window are the hardest to reverse later. Here’s the order to take them in.
What happens when
Three months before your birthday month
Your Initial Enrollment Period opens. Starting here means your coverage can begin the month you turn 65, with no gap and no penalty.
Decide whether to take Part B now
Still working with employer coverage? You may be able to delay without penalty, but it depends on the size of your employer. Getting this wrong creates a permanent surcharge.
Choose your path: Advantage or Supplement
The single biggest decision. Your six-month Medigap open enrollment starts when Part B begins, and medical underwriting is generally waived during it. Later it may not be, and that matters enormously if your health changes.
Match a drug plan to your prescriptions
We run your actual medication list against each plan’s formulary and pharmacy network, not a generic estimate.
Enroll, then review every fall
Coverage begins. From then on, a short annual check confirms your plan is still the right one for the year ahead.
The Part B decision if you're still working
This is where people get hurt, and the damage is permanent, so it’s worth being careful.
If you work for a larger employer and their group plan is creditable, you can usually delay Part B without penalty and enroll later through a Special Enrollment Period. If your employer is small, Medicare generally becomes the primary payer at 65 and delaying can leave you badly exposed.
Retiree coverage and COBRA are not the same as active employer coverage for these purposes, and that distinction trips people up regularly.
Bring these to the appointment
- Your Medicare card, or your Social Security details if you haven’t enrolled
- A list of your prescriptions with dosages
- The names of the doctors you want to keep
- Your employer plan’s summary of benefits, if you’re still working
- Any letters you’ve received from Medicare or a carrier
Why the underwriting window matters
During your initial Medigap open enrollment, a Supplement carrier generally cannot turn you down or charge you more because of your health history. That protection is time-limited.
Later on, if you want to move from a Medicare Advantage plan to a Supplement, you may have to answer health questions — and you can be declined. People who develop a condition after choosing Advantage sometimes find the door has closed.
None of that makes Advantage the wrong choice. Plenty of people are better served by it. But it should be a decision you make knowingly rather than one you discover later.
Turning 65 this year?
Start three months before your birthday month. A single appointment usually settles it.