Medicare Enrollment at 65: Key Questions to Ask

Sep 26, 2025

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Meredith Dean

RICP®

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If you are approaching 65 years of age, you may have noticed that you are receiving a lot more mail these days. Not from relatives or friends, but from Medicare Advantage companies eager for you to enroll in their plans. You may also notice more targeted television commercials with the same messaging.

The challenge with all this noise is it typically comes only from Medicare Advantage insurance companies. It doesn’t provide you all the information you need to make an informed decision. To complicate things further,  Medicare agents and brokers are also compensated with higher commissions for enrolling people into one of these Medicare Advantage Plans (Part C) versus Medigap (Supplement) plans paired with a standalone drug plan.

Many people are unaware of the differences between Medicare Advantage plans and original Medicare. The government provides limited education on these differences, which makes it especially important to know what questions to ask before making a decision. As you are approaching Medicare age and considering your options, start by asking yourself these questions:

When do I need to sign up for Medicare?

Your initial enrollment period is spread out over seven months:

  • You have the 3 months before your birth month
  • Your birth month
  • 3 months after your birth month.

For someone born in September, your enrollment window runs June through December. Missing this period can lead to penalties or delays in coverage.

Do I need to sign up if I have employer coverage?

This question depends on whether your employer plan is considered creditable coverage, meaning it is as good as Medicare.  The best way to confirm this is to contact someone in your company’s HR department or the plan administrator.

What if I have COBRA Coverage?

This is a common mistake.  COBRA is generally not considered creditable for Medicare Part B or Part D. Relying on COBRA alone could expose you to lifetime penalties for Part B premiums and prescription drug coverage. However, if you have COBRA and you’re eligible for Medicare, COBRA may only pay a small portion of your medical costs. You generally aren’t eligible for a Special Enrollment Period to sign up for Medicare when that COBRA coverage ends. (Source: Medicare & You 2026)

Why do some people pay more for Medicare?

Medicare looks back two years at your tax return to determine if you will pay an increased premium for Part B and Part D. This additional charge is based on income and is called IRMAA (Income-Related Monthly Adjustment Amount).

In 2025, Medicare will look at your 2023 tax return.  You may qualify to appeal if you’ve experienced a life-changing event such as retirement, a work reduction, divorce, or the death of a spouse, and a few others. Filing the appropriate Medicare appeal form can lower your premium back to the standard rate.

What are Medicare Advantage plans (Part C)?

Medicare Advantage plans combine Part A, Part B, and Part D. These plans are similar to an HMO or PPO Plan. Medicare Advantage plans have network restrictions, copays/coinsurances, max-out-of-pocket limits, some added benefits like dental, vision, and gym memberships, and some of these plans require referrals from your primary care provider before you can see a specialist.

You must be enrolled in Part A and Part B of Medicare to enroll into a Medicare Advantage Plan.

What are Medigap (AKA Supplement) plans?

Original Medicare doesn’t pay all the cost for covered health care services and supplies. Medicare Medigap (Supplement) Insurance policies sold by private insurance companies can help cover some of the remaining healthcare costs for covered services and supplies, such as copayments, coinsurance, and deductibles.

Medigap insurance is especially valuable if having nationwide access to providers and facilities is important to you. In most cases, you don’t need a referral to use a specialist. You must be enrolled in Part A and Part B of Medicare to purchase Medigap (Supplement) insurance.

Can I switch back and forth between Medicare Advantage plans and Original Medicare + Medigap (Supplement) Insurance?

The short answer is, maybe, but there are important limitations and rules to consider:

Switching from Medicare Advantage to Original Medicare + Medigap: You can generally do this during specific enrollment periods (like the Annual Enrollment Period, Oct 15–Dec 7), but you may not be guaranteed acceptance into a Medigap plan unless you’re in a protected situation (like your first year in a Medicare Advantage plan — called a “trial right”). Outside of those rights, insurers can deny coverage or charge more based on your health.

Switching from Original Medicare + Medigap to Medicare Advantage: You can do this during the Annual Enrollment Period, and you typically don’t need medical underwriting — you’re generally accepted into an Advantage plan regardless of your health.

So while switching is possible, going back to Medigap can be much harder than switching to Medicare Advantage. Planning ahead is key.

Why these choices matter

Some of the decisions that you make at the start of Medicare can affect your health coverage options for the rest of your life. Medicare mistakes can be costly, but they can be avoided with the right guidance.

People may not always think to bring this topic to their financial advisor, but at TCI, we believe it’s critical to your peace of mind, retirement happiness, and long-term goals.

We are only scratching the surface in this brief post. If you are approaching 65 and wondering how Medicare fits into your plan, reach out to your Advisor so we can talk through it together.

TCI Wealth Advisors, Inc. is an investment advisor registered with the Securities Exchange Commission. This material is provided for information and education only.  TCI does not sell insurance and is not associated with or endorsed by Medicare or the Centers for Medicare or Medicaid Services.  If there is a specific question regarding Medicare coverage, costs or premium options you should contact your Medicare Insurance Broker.  

Meet the Author

Meredith Dean,

RICP®

See Bio
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