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Are You Making These Common Medicare Enrollment Mistakes at 65?


Turning 65 is a huge milestone. It’s the age where many of us start dreaming about golf courses, beach sunsets, or finally finishing that DIY project in the garage. But it’s also the age when the "Medicare Mail Avalanche" starts hitting your mailbox.

If you’re turning 65 in 2026, you’re entering the Medicare world at a very interesting time. Rules are changing, drug costs are shifting, and the choices you make now can affect your wallet (and your health) for decades. At Solomon Estate and Wealth Planning, we see people get overwhelmed by the jargon every single day.

Let’s cut through the noise and look at the most common Medicare enrollment mistakes people make at 65: and more importantly, how you can avoid them.

1. The "I'll Do It Later" Trap (Timing Mistakes)

One of the biggest mistakes people make is thinking they can just sign up whenever they feel like it. Medicare has very strict enrollment windows, and missing them can lead to lifetime penalties.

Your Initial Enrollment Period (IEP) is a seven-month window: three months before you turn 65, the month you turn 65, and three months after. If you miss this, you might have to wait until the General Enrollment Period, and you could be hit with a late enrollment penalty for Part B and Part D that stays with you forever.

2026 Pro-Tip: If you are still working and have "creditable" coverage from an employer with 20 or more employees, you might be able to delay. But don't just assume! Always verify with a pro to make sure your current plan counts, or you’ll be in for a nasty surprise when you finally do retire.

2. Choosing a Plan Based ONLY on the Premium

We all love the sound of a "$0 Premium" plan. It sounds like a steal, right? But in the Medicare world, you usually get what you pay for. Many people flock to Medicare Advantage plans because of the low monthly cost, but they forget to look at the "back-end" costs.

A close-up of a calculator and financial documents, representing the careful analysis needed for Medicare costs beyond just premiums.

When you choose a plan based only on the premium, you might be overlooking:

  • High Co-pays: That $0 premium plan might charge you $300 every time you need an MRI.

  • Out-of-Pocket Maximums: Some plans have limits as high as $8,000 or more for 2026.

  • Network Restrictions: If your favorite doctor isn't "in-network," you’re paying full price.

At Solomon Estate, we help our clients run a "total cost" analysis. We look at the premiums plus the expected co-pays plus the potential "worst-case scenario" costs to find the real winner for your budget. You can book a Medicare consultation here to have us run these numbers for you.

3. Ignoring the New 2026 Medicare Part D Changes

2026 is a landmark year for prescription drug coverage. Thanks to recent legislation, there is now a hard annual out-of-pocket cap of $2,000 for covered Part D drugs.

A 3D graphic showing a $2,000 cap shield, representing the new 2026 Medicare Part D drug spending limit.

While this is great news for people with high-cost medications, it also means the "landscape" of plans has shifted.

  • The "Smoothing" Program: Starting in 2026, you have the option to spread that $2,000 out over the year in monthly installments rather than paying a huge chunk at the pharmacy in January. This is called the Medicare Prescription Payment Plan.

  • The Premium Hike: Because the drug cap is lower, some insurers are raising their Part D premiums to compensate.

Don't just stick with the plan you had last year. In 2026, your "old faithful" drug plan might have changed its formulary (the list of drugs it covers) or jacked up its price.

4. Medigap vs. Medicare Advantage: Making the Wrong Choice for Your Lifestyle

This is the "Big Debate." Do you go with Original Medicare + a Medigap Supplement, or do you choose a Medicare Advantage (Part C) plan?

An illustration of a provider network (Advantage) vs. an open road of medical icons (Supplement), showing the trade-off between extras and freedom of choice.

Here is the breakdown for 2026:

  • Medicare Supplement (Medigap):

  • Medicare Advantage:

If you’re a "snowbird" who spends half the year in Florida and the other half in Alabama, a narrow-network Advantage plan could be a disaster. On the other hand, if you’re very healthy and want to save on premiums, Advantage might be a great fit. It’s all about your lifestyle.

5. Thinking Your Doctor Will "Just Be Covered"

This is perhaps the most heartbreaking mistake. We’ve seen folks sign up for a plan, walk into their doctor’s office of 20 years, and find out they are no longer in-network.

In 2026, many Medicare Advantage networks are getting tighter. Even if your doctor was in-network last year, they might not be this year. Always, always check the current provider directory for 2026 before hitting "enroll."

The Solomon Estate Checklist for 2026 Enrollment

Ready to get started? Here is your quick checklist to make sure you’re on the right track:

  1. Check your Part B Premium: For 2026, the standard Part B premium is $202.90 per month. Make sure your budget accounts for this!

  2. Audit your Meds: List every prescription you take. Use the Medicare Plan Finder (or better yet, give us a call) to see which plan covers your specific meds at the lowest cost under the new $2,000 cap.

  3. The Doctor Test: Call your specialist’s office and ask: "Do you accept this specific 2026 Medicare Advantage plan?" (Don't just ask if they "take Medicare": that's different!)

  4. Look at the "Max Out of Pocket": If you had a bad health year, could you afford the $7,000+ maximum out-of-pocket on that Advantage plan? If not, a Supplement (Medigap) might be safer.

  5. Think about the Future: It’s often easier to get into a Medigap plan when you first turn 65. If you start with Advantage and try to switch to Medigap later, you might have to go through "medical underwriting," and they could deny you if you have health issues.

Angelique Solomon talking to a couple in a modern office about their retirement and Medicare planning.

How We Can Help

Medicare is not a "one-size-fits-all" deal. It’s a puzzle, and the pieces change every year. At Solomon Estate and Wealth Planning, we specialize in helping people navigate these transitions: whether it’s rolling over your 401(k) as you retire or finding the Medicare plan that lets you keep your doctor.

Don't go it alone and risk a lifetime of penalties or high costs. Let’s sit down and look at your specific situation together. We can help you integrate your healthcare choices into your overall retirement planning strategy.

Angelique Solomon, CEO of Solomon Estate and Wealth Planning, ready to help you with your Medicare and retirement needs.

Ready to stop the guessing game? Give us a call at (334) 459-8264 or visit our blog for more tips on staying retirement-ready in 2026.

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

NPN: 20332097 States: AL, FL, GA, SC, VA, TX, OHIO Designations: L&H Phone: (334) 459-8264 Website:https://www.angeliquebenefits.com/

 
 
 

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