Turning 65? Here's Everything You Need to Know About Medicare in 2026
Turning 65? Here’s Everything You Need to Know About Medicare in 2026
Turning 65 is a milestone worth celebrating — but it also comes with a to-do list that most people aren’t prepared for. Medicare is one of the most important financial and healthcare decisions you’ll make in retirement, and the rules around enrollment, plan choices, and costs can feel overwhelming if you’re navigating them alone.
The good news? Once you understand how the pieces fit together, Medicare doesn’t have to be complicated. In this guide, I’ll walk you through everything you need to know — your enrollment window, what each part of Medicare covers, how to choose the right plan, and the most common mistakes I see people make every year as a licensed independent Medicare advisor in Oregon.
Let’s start at the very beginning.
Your 7-Month Initial Enrollment Window — And Why It Matters
When you turn 65, you have a 7-month Initial Enrollment Period (IEP) to sign up for Medicare. This window is not flexible — it’s set by the federal government, and missing it can cost you for years to come.
Here’s how the 7-month window breaks down:
- 3 months before your 65th birthday month
- Your birthday month itself
- 3 months after your birthday month
Example: If your birthday is September 15, your IEP runs from June 1 through December 31.
When you enroll matters — not just whether you enroll
Timing within your IEP affects when your coverage actually starts:
| When You Enroll | Coverage Starts |
|---|---|
| 1–3 months before your birthday | 1st of your birthday month |
| Your birthday month | 1st of the following month |
| 1 month after your birthday | 2 months after enrollment |
| 2–3 months after your birthday | 3 months after enrollment |
The bottom line: Enrolling in the 3 months before your birthday gets you the fastest coverage start. Waiting until your birthday month or after creates a gap.
What happens if you miss your IEP?
If you miss your Initial Enrollment Period without a qualifying exception, you’ll face two consequences:
- Late enrollment penalties — Your Part B premium increases by 10% for every 12-month period you were eligible but didn’t enroll. Those penalties are permanent and follow you for life.
- A wait until the General Enrollment Period (GEP) — You can only sign up between January 1 and March 31 each year, with coverage starting July 1.
Missing this window is one of the most expensive mistakes I see, and it’s entirely avoidable with the right guidance.
Medicare Part A vs. Part B: What Each Covers (and What It Costs)
Medicare is divided into parts, and understanding what each covers is essential before you choose a plan.
Medicare Part A — Hospital Insurance
Part A covers:
- Inpatient hospital stays
- Skilled nursing facility care (following a qualifying hospital stay)
- Hospice care
- Some home health care
Cost in 2026:
- Premium: $0 for most people (if you or your spouse worked and paid Medicare taxes for at least 10 years / 40 quarters)
- Inpatient deductible: $1,736 per benefit period — not per year
- Days 61–90 coinsurance: $434 per day
- Days 91–150 (lifetime reserve days): $868 per day
Note that the Part A deductible resets with each new benefit period, not each calendar year. If you have multiple hospital stays, you could owe this deductible more than once in a year.
Medicare Part B — Medical Insurance
Part B covers:
- Doctor visits and outpatient services
- Preventive care (annual wellness visits, screenings, vaccines)
- Durable medical equipment
- Outpatient mental health services
- Most medically necessary services not covered by Part A
Cost in 2026:
- Premium: $202.90/month (standard; higher-income enrollees pay more due to IRMAA surcharges)
- Annual deductible: $283
- Coinsurance: 20% of Medicare-approved costs after the deductible — with no annual out-of-pocket cap under Original Medicare alone
That 20% coinsurance with no ceiling is the most important number to understand. A $200,000 hospital stay leaves you responsible for $40,000 under Original Medicare by itself. That’s why most people choose supplemental coverage — which brings us to the three big choices.
The 3 Big Medicare Choices You’ll Need to Make
Once you’re enrolled in Parts A and B, you have three paths forward:
Option 1: Original Medicare + a Medigap (Supplement) Policy
You keep Original Medicare as your primary insurance and add a private Medigap policy to cover most or all of the out-of-pocket costs Original Medicare doesn’t pay. You’ll also want a Part D (prescription drug) plan.
Option 2: Medicare Advantage (Part C)
Instead of using Original Medicare directly, you enroll in an all-in-one private health plan that bundles Parts A, B, and usually D — often with extra benefits like dental, vision, and hearing.
Option 3: Original Medicare + Part D Only (No Supplement)
You keep Original Medicare with a drug plan but no supplemental coverage. This leaves you exposed to the 20% coinsurance with no cap. This option works best for people with very limited budgets and excellent health, but it carries real financial risk.
Most people choose Option 1 or Option 2. Let’s dig into that comparison.
Medicare Advantage vs. Medigap: The Real Comparison
This is the most important decision most people turning 65 will make, and there’s no single “right” answer. The best choice depends on your health, finances, and lifestyle.
Monthly Premiums
| Medicare Advantage | Medigap (Plan G) | |
|---|---|---|
| Part B premium | $202.90 | $202.90 |
| Plan premium | Often $0–$50/month | $100–$300+/month |
| Total monthly cost | ~$203–$253 | ~$303–$503+ |
Medicare Advantage plans often look less expensive month-to-month — and for healthy years, they often are. But the real cost comparison happens when you actually need care.
Out-of-Pocket Costs When You Need Care
- Medicare Advantage: Plans have a federally mandated out-of-pocket maximum — up to $9,350 in 2026 for in-network services. But you’ll face copays and coinsurance for every doctor visit, specialist, procedure, and hospital stay along the way.
- Medigap Plan G: After you pay the $283 Part B deductible once per year, Plan G covers 100% of your Medicare-approved costs — no copays, no coinsurance, no surprises.
Provider Networks
- Medicare Advantage: You typically must use in-network providers. Seeing out-of-network doctors often costs significantly more, and some plans require referrals to see specialists.
- Medigap: You can see any doctor or specialist in the U.S. who accepts Medicare — no referrals, no network restrictions. This is particularly valuable if you travel frequently, have a complex condition, or want to see specialists at major medical centers.
Extra Benefits
- Medicare Advantage: Many plans include dental, vision, hearing, fitness memberships (like SilverSneakers), and even some over-the-counter allowances. These extras are real value — but they vary widely by plan and can change year to year.
- Medigap: No extra benefits beyond filling Medicare’s cost gaps. You’d add a standalone Part D drug plan and potentially a dental/vision plan separately.
The Bottom Line Comparison
| Medicare Advantage | Medigap | |
|---|---|---|
| Lower monthly premium | ✅ | ❌ |
| Predictable costs when sick | ❌ | ✅ |
| Freedom to see any Medicare doctor | ❌ | ✅ |
| Extra benefits (dental, vision) | ✅ | ❌ |
| Best for healthy people on a budget | ✅ | ❌ |
| Best for people with chronic conditions or who travel | ❌ | ✅ |
My honest take: Medigap offers the most financial certainty and freedom. Medicare Advantage can be an excellent value for the right person. The key is matching the plan to your situation — not choosing based on what your neighbor or brother-in-law has.
What If You’re Still Working at 65? Understanding the Special Enrollment Period
Many people continue working past 65 and have employer-sponsored health coverage. The good news: you don’t have to enroll in Medicare right away — as long as your employer coverage is considered creditable (meaning it’s at least as good as Medicare).
Here’s what you need to know:
- You can delay Part B (and Part D) without penalty as long as you’re covered by an active employer group health plan based on current employment (yours or a spouse’s).
- COBRA and retiree coverage do not qualify as creditable coverage for this purpose. If that’s what you have at 65, you need to enroll during your IEP.
- When your employer coverage ends, you have an 8-month Special Enrollment Period (SEP) to enroll in Part B without penalty — starting the month after your employment or employer coverage ends, whichever comes first.
Important: Don’t wait until the last minute. The SEP is 8 months, but Medigap insurers can use medical underwriting if you enroll outside your initial guaranteed-issue window. Timing your enrollment correctly protects your right to the plan you want.
If you’re in this situation, I strongly recommend a one-on-one conversation before you make any decisions. Getting this wrong can be costly and hard to undo.
Medicare in Oregon: What You Should Know
Oregon has one of the most developed Medicare markets in the Pacific Northwest, which means you have excellent options — but also more choices to navigate.
Key Oregon Medicare facts for 2026:
- Approximately 831,000 Oregonians are age 65 or older — nearly 20% of the state’s population
- Oregon has a strong Medicare Advantage market with plans available from major carriers including Kaiser Permanente, UnitedHealthcare (AARP), Aetna, Humana, and regional options
- 12 standardized Medigap plans are available in Oregon, including high-deductible options
- 10 standalone Part D plans are available for those on Original Medicare + Medigap
- Oregon’s SHIBA (Senior Health Insurance Benefits Assistance) program offers free, unbiased Medicare counseling — a great resource, though counselors can’t recommend specific plans or carriers
One Oregon-specific note: Kaiser Permanente has a strong regional presence and consistently earns high CMS star ratings for its Medicare Advantage plans. However, Kaiser operates as an HMO — meaning you must use Kaiser providers. That’s a significant trade-off if your current doctors are outside the Kaiser network.
As an independent broker, I work with all major carriers in Oregon and can compare plans across the full market — not just one company’s lineup.
The Biggest Medicare Mistakes People Make at 65
After working with hundreds of clients navigating Medicare, these are the errors I see most often:
1. Missing the Initial Enrollment Period
The most expensive mistake. Even one month of delay can trigger a permanent penalty. Set a calendar reminder 4 months before your 65th birthday.
2. Assuming Medicare Covers Everything
Original Medicare does not cover dental, vision, hearing, or long-term care. Many people are shocked to discover these gaps after they enroll.
3. Choosing a Plan Based on Premium Alone
The cheapest monthly premium isn’t always the least expensive plan. A $0 premium Medicare Advantage plan with high copays can cost far more than a $150/month Medigap plan if you have a serious health event.
4. Not Reviewing Your Plan Annually
Medicare plans change every year — premiums, formularies, networks, and benefits all shift on January 1. The Annual Enrollment Period (October 15 – December 7) exists for a reason. Review your plan every year.
5. Relying on a Captive Agent or 1-800-MEDICARE
Captive agents can only offer plans from one carrier. The 1-800-MEDICARE line doesn’t make plan recommendations. Working with an independent broker who represents multiple carriers gives you a true, unbiased comparison.
6. Forgetting About IRMAA
If your income exceeds $106,000 (individual) or $212,000 (married filing jointly), you’ll pay higher Part B and Part D premiums due to IRMAA surcharges. This catches a lot of recently retired professionals off guard — especially in the year they retire, when their prior-year income is still high.
7. Delaying Medicare Because of COBRA or Retiree Coverage
COBRA and retiree health plans are not creditable employer coverage under Medicare rules. Relying on them to delay enrollment can trigger late penalties. Always verify your coverage type before deciding to delay.
Ready to Make the Right Medicare Decision?
Medicare is one of the most consequential financial decisions you’ll make as you approach retirement — and it doesn’t have to be stressful. With the right guidance, you can choose a plan that fits your health, your budget, and your lifestyle with complete confidence.
I’m Rodney Cummings, a licensed independent insurance advisor serving Oregon and clients nationwide. As an RSSA® (Retirement Income Certified Professional for Social Security) and Medicare specialist, I work with a wide portfolio of carriers to find the plan that’s right for you — not the plan that pays the highest commission.
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Rodney Cummings is a licensed independent insurance advisor in Oregon (License #18847712). This article is for informational purposes only and does not constitute legal, tax, or financial advice. Medicare plan availability and costs vary by location and are subject to change annually. Always verify current plan details with a licensed advisor or at Medicare.gov.