When to Enroll in Medicare: The Complete T65 Checklist
When to Enroll in Medicare: The Complete T65 Checklist
Turning 65 is a milestone — and so is Medicare enrollment. But if you miss a deadline or sign up for the wrong plan, you could face lifetime premium penalties or a gap in coverage that costs you thousands.
This checklist breaks down everything you need to know before your 65th birthday.
Why the T65 Window Matters
Medicare has an Initial Enrollment Period (IEP) that spans 7 months:
- 3 months before the month you turn 65
- The month you turn 65
- 3 months after the month you turn 65
Miss this window without a valid reason, and you’ll pay a permanent 10% late enrollment penalty on your Part B premium for every 12-month period you delayed. On the 2024 standard Part B premium of $174.70/month, that adds up fast.
The T65 Enrollment Checklist
✅ 6–9 Months Before Your Birthday
- Gather your Social Security information. If you’re already receiving Social Security benefits, you may be automatically enrolled in Part A and Part B. Confirm this at SSA.gov.
- Check your employer coverage. Are you or your spouse still working with employer-sponsored health insurance? If the employer has 20+ employees, you may be able to delay Part B without penalty.
- Estimate your prescriptions. List all current medications. You’ll use this when comparing Part D (drug coverage) plans.
- Research your doctors. Are your current doctors in Medicare networks? Some specialists don’t accept Medicare assignment — check now, not after you enroll.
✅ 3 Months Before Your Birthday
- Decide between Original Medicare and Medicare Advantage.
- Original Medicare (Parts A + B) gives you access to nearly every doctor in the country. Pair it with a Medigap Supplement for predictable costs.
- Medicare Advantage (Part C) bundles everything into one plan, often with dental and vision. Trade-off: network restrictions.
- Compare Medigap plans (if choosing Original Medicare). Plans F, G, and N are the most popular. Plan G is now the most comprehensive available to new enrollees.
- Get your Medicare number. This arrives by mail before your birthday month. Don’t lose it.
- Schedule a free consultation. A licensed Medicare specialist can compare every plan available in your zip code at no cost to you.
✅ The Month You Turn 65
- Enroll in Part B (if not automatic). Log in at Medicare.gov or call 1-800-MEDICARE.
- Choose and enroll in a Supplement or Advantage plan. This is the most important decision — get help if you’re unsure.
- Choose a Part D drug plan. Even if you take no prescriptions, enrolling in a low-cost plan protects you from the late enrollment penalty.
- Coordinate any transition from employer coverage. Get written confirmation from your employer’s HR department about when your current coverage ends.
✅ After Enrollment
- Notify your doctors of your Medicare number.
- Set up your MyMedicare.gov account. You can track claims and manage your coverage online.
- Review your plan during Annual Enrollment (Oct 15–Dec 7). Plans change every year. What was best last year may not be best next year.
The 5 Biggest Medicare Enrollment Mistakes
Mistake #1: Assuming Medicare is free. Part A is free for most people, but Part B has a monthly premium ($174.70+ in 2024). Medigap supplements add additional cost.
Mistake #2: Waiting until you need it. Once you’re sick is the worst time to shop for coverage. You can’t be turned down during your initial enrollment period, but you can be after.
Mistake #3: Choosing Advantage for the extras without reading the fine print. Dental and vision benefits often have annual caps of $500–$1,500. Know what you’re actually getting.
Mistake #4: Not considering your travel habits. Medicare Advantage plans are network-based. If you travel or split time between states, Original Medicare + a Supplement gives you nationwide freedom.
Mistake #5: Going it alone. Medicare has 47+ Medigap plans and dozens of Advantage plans in most zip codes. A licensed broker represents all carriers and compares everything in one conversation — at no cost to you.
What Does Medicare Actually Cover?
| Coverage | Part A (Hospital) | Part B (Medical) |
|---|---|---|
| Hospital stays | ✅ Yes | ❌ No |
| Doctor visits | ❌ No | ✅ Yes |
| Surgeries | ✅ Yes | ✅ Yes |
| Preventive care | ❌ No | ✅ Yes |
| Skilled nursing | ✅ Limited | ❌ No |
| Prescription drugs | ❌ No | ❌ No (need Part D) |
| Dental | ❌ No | ❌ No |
| Vision | ❌ No | ❌ No |
This is why most people choose either a Supplement (Medigap) or Medicare Advantage — to fill these gaps.
Get a Free Medicare Review
Legacy Wealth Services works with 20+ Medicare carriers across Oregon and 25+ states. Our licensed specialists compare every plan available in your area — including Supplements, Advantage plans, and Part D drug plans — and help you choose the right fit for your budget, doctors, and prescriptions.
Ready to schedule your free Medicare review? Call us at 503-832-8555 or visit legacywealthservices.com.
Rodney Cummings is a licensed Medicare specialist serving clients nationwide from Happy Valley, Oregon.