Turning 65 may be one of the most significant healthcare and financial milestones in your life. Once you become eligible for Medicare, you need to make decisions about your long-term healthcare coverage. The Medicare plan you select can have a major impact on the rest of your life because some Medicare decisions are difficult to reverse.
This guide gives you a comprehensive overview of what you need to do before you turn 65, whether you’re already retired or plan to keep working. And if you need help comparing specific plans, Chapter’s licensed Medicare Advisors offer free Medicare support, helping you compare every option to find the plan that best fits your health and financial needs.
Key takeaways:
Turning 65 triggers Medicare eligibility, but you may choose to delay enrollment if you’re still working.
Healthcare is one of the largest expenses in retirement. Understanding your options helps you avoid penalties, overpaying, and unexpected out-of-pocket costs.
Avoid penalties by making sure you know when you’re eligible and what the requirements are for delaying coverage.
Why is turning 65 an important healthcare milestone?
Although some people with disabilities qualify early, most people become eligible for Medicare when they turn 65. But should you enroll right away? If so, what plan should you choose?
Should you enroll in Medicare now or delay it until you retire?
Most people enroll in Medicare plans Part A and Part B at age 65, which cover about 80% of the costs for covered care. If you meet the age requirement and you or your spouse paid Medicare taxes for 10 or more years, you’ll pay nothing for Part A coverage. Most people need to pay the standard Part B monthly premium ($202.90 in 2026).
If you or your spouse still work and have a qualifying employer group health plan, you can delay Medicare Part B enrollment without penalty. Your employer-coverage qualifies if your employer has 20 or more employees. That said, you should compare your employer coverage with Medicare to see if you can save with Medicare.
Should you get supplementary coverage?
Original Medicare only pays for about 80% of the costs of covered care. Medigap, Medicare Advantage, and Part D are private plans that can help cover what Original Medicare doesn’t, such as out-of-pocket costs, prescriptions, dental, and vision. Most people choose to add at least one other type of coverage to reduce gaps in their retiree health coverage.
How does employment status impact your health insurance options at age 65?
Your health insurance checklist for turning 65 looks different, depending on if you choose to retire or keep working.
If you’re retired at 65
If you’re preparing for retirement at age 65, you should plan to enroll in Medicare.
First, sign up for Original Medicare. Enroll in Part A and Part B during your Initial Enrollment Period (IEP) to avoid coverage gaps and late penalties.
Then, choose supplemental coverage. Decide between adding Medigap or switching to Medicare Advantage. Note that if you choose Medicare Advantage but want to switch to Medigap later, there’s a chance you could be denied based on your health history. You will also need to look into prescription coverage (Part D). Part D is included in many Medicare Advantage plans and can also be purchased as a standalone plan.
If you’re still working at 65
People still working after they turn 65 have different Medicare enrollment decisions to make.
First, you should enroll in Medicare Part A. If you or your spouse have paid Medicare taxes for at least 10 years, you can get Part A for free. If you still have coverage through work, Part A can act as a secondary payer to help cover out-of-pocket costs left unpaid by your primary plan.
If you don’t qualify for premium-free Part A, you’ll need to pay for Part A premiums, and when you enroll matters. If you enroll it after your Initial Enrollment Period closes, your monthly premium will go up 10% (unless you meet conditions for a Special Enrollment Period).
When it comes to Part B, compare your employer coverage with Medicare to see which one makes sense for your health and financial situation. If your employer has 19 or fewer employees, you should enroll in Part B to avoid the Part B penalty.
If your employer has 20 or more employees, you can delay enrolling in Part B without penalty. After you retire, you’re eligible for an eight-month Special Enrollment Period. If you miss this window, you’ll pay an extra 10% for each year you could’ve enrolled in Part B but didn’t.
Some employers offer special retiree healthcare coverage after you leave your job. But these plans often require you to enroll in both Part A and Part B to be fully covered. Make sure you carefully review all documentation and understand your options before you make enrollment decisions. If you need help figuring out which plan is best for you, Chapter’s licensed Medicare Advisors can help.
How should you compare Medicare coverage options before turning 65?
Choosing the right Medicare plan depends on your health and financial situation.
| Coverage option | What it includes | What to check before choosing |
|---|---|---|
| Original Medicare only | This covers hospital and outpatient care. There is no limit on out-of-pocket costs. | Are you comfortable with uncapped out-of-pocket costs? Do you need prescription drug coverage or dental, vision, and hearing care? |
| Original Medicare + Part D coverage | This combination adds prescription drug coverage, but there is still no out-of-pocket cap for medical costs. | Are your medications covered? Consider adding a Medigap plan to lower or eliminate out-of-pocket costs. |
| Original Medicare + Medigap + Part D coverage | This combination includes prescription drug coverage and significantly reduces out-of-pocket costs. | If you don’t sign up for Medigap during your Medigap Open Enrollment Period, you could be denied coverage later. |
| Medicare Advantage (Part C) | This bundles Part A, Part B, and usually Part D into one plan along with extra benefits that vary by plan. | Are your preferred doctors in network? Are your prescriptions covered? |
| Employer or retiree health coverage | This is coverage through a current or former employer. Note that many retiree health plans still require you to enroll in Part A and Part B. | Is your coverage primary or secondary to Medicare? Confirm this with your benefits administrator before delaying Medicare enrollment. |
Chapter can make comparing plans easier by checking that your doctors and prescriptions are covered and helping you understand your estimated costs.
What financial decisions should you make before turning 65?
Healthcare can be one of the largest practical expenses in retirement. Fidelity estimates that the average senior citizen may need $172,500 to cover healthcare costs in retirement—and that doesn’t include long-term care.
Start here when assessing your retirement finance health:
Social Security strategy: If you receive Social Security benefits before age 65, you’ll be automatically enrolled in Part A and Part B. Your premiums for Part B may be deducted from your benefits. If you don’t receive Social Security benefits, it may be worth delaying them. Your monthly benefit can increase by around 8% each year until you turn 70. If you delay claiming Social Security, you’ll need to enroll in Medicare via the SSA website.
Retirement income plan: Your retirement income level can affect how much you pay for Medicare Part B and Part D. Higher earners can expect to pay more according to the Income-Related Monthly Adjustment Amount (IRMAA).
Additional income and tax considerations: Part-time work or other income sources can impact your tax and IRMAA thresholds.
Long-term care needs: Medicare does not cover most long-term care. Evaluating long-term care insurance options before you turn 65 is a good idea, as premiums increase with age and some conditions may disqualify you from coverage.
What doctors, prescriptions, and care needs should you review before 65?
Reviewing the care you currently need before you turn 65 gives you the information you need to compare coverage options. A plan that seems reasonable and affordable on paper may cost you more if your providers are out of network or your medications are on a high-cost tier. Always keep in mind that your healthcare needs can change. Ask your Medicare agent questions about how the coverage you choose today will work if your health changes.
Make sure to:
Verify provider networks: List every doctor, specialist, and hospital you see regularly. If you are considering Medicare Advantage, confirm each provider is in network with the plan you choose. Any provider that accepts Medicare is covered with a Medigap plan.
Review your prescriptions: Write down every medication, including dosage. Check how each drug is covered under the plans you are comparing.
Complete outstanding care: Schedule any preventative screenings, dental work, and specialist visits covered under your current plan before it expires. Once you’re enrolled, Medicare Part B offers a complimentary “Welcome to Medicare” visit during your first 12 months of coverage. After this, you get a free Wellness Visit one each year as well as a number of other preventative services, including many vaccines and screenings.
Get Medicare guidance before you turn 65
The healthcare and retirement planning decisions you make when you turn 65 can affect your healthcare costs and coverage options for years. Chapter can review your coverage options in under 20 minutes and help ensure you won’t face penalties. Whether you need a full breakdown of your options or just want to work through one specific question, Chapter’s licensed, independent Medicare Advisors can make picking a plan a little easier.
Chat with us today at 855-900-2427 or book an appointment ahead of time. We’re here to help.
Sources:
Centers for Medicare & Medicaid Services. (n.d.). When can I sign up for Medicare? Medicare.gov. https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-can-i-sign-up-for-medicare
Centers for Medicare & Medicaid Services. (n.d.). Medicare & working past 65. Medicare.gov. https://www.medicare.gov/basics/get-started-with-medicare/medicare-basics/working-past-65
Centers for Medicare & Medicaid Services. (2026). Medicare & you 2026. https://www.medicare.gov/medicare-and-you
Fidelity Investments. (2023). How to plan for health care costs in retirement. https://www.fidelity.com/viewpoints/personal-finance/plan-for-rising-health-care-costs
Internal Revenue Service. (n.d.). Health savings accounts and other tax-favored health plans. IRS.gov. https://www.irs.gov/publications/p969
Social Security Administration. (n.d.). When to sign up for Medicare. SSA.gov. https://www.ssa.gov/medicare/plan/when-to-sign-up
