What Are the Biggest Medicare Enrollment Mistakes in North Carolina—and How Can You Avoid Them?

Learn the top Medicare enrollment mistakes North Carolinians make, from missed deadlines to plan pitfalls, and how to avoid penalties or coverage gaps. Billy Jordan of The Jordan Insurance Agency breaks it all down.

In this episode

• How missing your Medicare window leads to penalties and coverage gaps
• Why COBRA and small employer plans can trigger costly Medicare mistakes
• How your first plan choice affects your future Medicare options in North Carolina

Read the full guide: The Biggest Mistakes Seniors Make When Enrolling in Medicare and How to Avoid Them

Billy Jordan is a licensed insurance agent (NPN 8699876) with The Jordan Insurance Agency, based in Charlotte, North Carolina. Voices in this episode are AI-generated, including Billy's, from a script reviewed and approved by Billy Jordan, a licensed insurance agent. General education only, not advice for your specific situation.

Not affiliated with or endorsed by Medicare or any government agency.

Tanya (AI host): I keep hearing about people getting hit with Medicare penalties or losing out on coverage just because they missed a deadline—what are the biggest mistakes folks make when signing up for Medicare, and how can you avoid them if you’re in North Carolina? Stick with us and we’ll break down the most common pitfalls.

Tanya (AI host): Welcome to Smart Coverage. Real Advice., the insurance podcast from The Jordan Insurance Agency. I'm Tanya, your host, and I'm here with Billy Jordan, a licensed insurance agent and the president of The Jordan Insurance Agency.

Billy Jordan: Always a pleasure, Tanya. A quick disclaimer: we're not affiliated with or endorsed by Medicare or any government agency, and this is general education, not advice for your situation. Now, let's get into it.

Tanya (AI host): Let’s start with the big one: what’s the most common—and costly—mistake people make when enrolling in Medicare?

Billy Jordan: The mistake is missing your Initial Enrollment Period when you turn sixty-five. That’s a seven-month window: three months before your birthday month, your birthday month itself, and three months after. If you miss it and don’t qualify for an exception, you can get stuck with lifetime penalties and coverage gaps. For example, if someone misses their window and goes thirty-six months without signing up for Part B, they’ll pay a thirty percent permanent penalty on their monthly Part B premium for as long as they have Medicare.

Tanya (AI host): Thirty percent, every month, for life? That’s steep. What about prescription drug coverage—are there penalties for that too?

Billy Jordan: Yes, there’s a separate penalty for Part D, which covers prescription drugs. If you go sixty-three days or more without Medicare drug coverage or other creditable drug coverage after your initial window, you’ll pay a penalty. It’s calculated as one percent of the national base beneficiary premium for every month you go without coverage, and it sticks with you as long as you have Medicare drug coverage.

Tanya (AI host): So if you miss your enrollment period, what happens next—do you just have to wait for the next year?

Billy Jordan: That’s right. If you miss your Initial Enrollment Period and don’t qualify for a Special Enrollment Period, you have to wait for the General Enrollment Period, which runs January first through March thirty-first each year. But here’s the catch: your coverage usually starts the month after you enroll, so you could have months with no insurance to cover doctor visits or hospital care.

Tanya (AI host): That could leave someone with a big gap if something unexpected happens. What’s one mistake you see people make when they’re still working at sixty-five?

Billy Jordan: The big trap here is assuming your job-based coverage always lets you delay Medicare without penalty. Whether you can delay safely depends on your employer’s size. If your employer has twenty or more employees, their group plan pays first and you can qualify for a penalty-free delay. But if the company has fewer than twenty employees, Medicare usually pays first. If you skip Part B in that case, your employer plan might refuse to pay for things like outpatient visits, and you’d be on the hook for the bills.

Tanya (AI host): So small business employees really need to double-check before they decide to wait. What about coverage like COBRA or retiree plans—do those count for delaying Medicare?

Billy Jordan: That’s a really common misconception. COBRA and retiree health plans do not count as active employment for Medicare’s enrollment rules. You generally get eight months after your employment or coverage ends, whichever comes first, to sign up for Part B without penalty. If you miss that, penalties and gaps apply. And here’s the mistake: people think COBRA protects them, but it doesn’t for Medicare Part B. Drug coverage under these plans might be creditable for Part D, but you have to check each part separately.

Tanya (AI host): I’ve heard that HSAs and Medicare don’t mix. What do people get wrong there?

Billy Jordan: Great question. Once you enroll in any part of Medicare—including premium-free Part A—you can’t contribute to a Health Savings Account anymore. If you sign up for Part A after you turn sixty-five, your start date is automatically backdated up to six months, but never before your sixty-fifth birthday month. That means you might accidentally over-contribute to your HSA and owe a six percent excise tax on the extra. The fix is to pull out the excess and any earnings by your tax return deadline, but a lot of people miss this detail.

Tanya (AI host): That could be a costly slip-up if you’re not careful with your timing. Switching gears, what about Medigap and Medicare Advantage plans—are there mistakes people make when choosing between those?

Billy Jordan: Absolutely. Many folks think they can just switch between Medicare Advantage and Medigap every year, but that’s not how it works. Your Medigap Open Enrollment Period is a one-time, six-month window that starts when you’re both sixty-five or older and enrolled in Part B. During that time, you can buy any Medigap plan without health questions. After that, unless you have a specific “trial right” or another protection, insurance companies can use medical underwriting and might deny you coverage.

Tanya (AI host): What’s a “trial right”? I don’t think a lot of people know about that.

Billy Jordan: A “trial right” gives you a special one-time chance. If you join a Medicare Advantage plan when you first get Medicare at sixty-five and decide within the first year it’s not right for you, you can drop it and buy a Medigap policy with no health questions asked. But once that year is up, or if you switch again later, you may not have that protection. People often assume they can always go back, but after the window closes, you might be locked out or face higher Medigap costs if you have health issues.

Tanya (AI host): So choosing a plan isn’t just about what you want this year—it can affect your options for years to come.

Billy Jordan: Exactly. And here’s a common mistake: people jump into a Medicare Advantage plan thinking they can just try it out, not realizing their Medigap open enrollment or trial right may not be there when they want to switch back. Always check your guaranteed-issue rights before making a change.

Tanya (AI host): Before someone enrolls, what should they double-check to avoid these headaches?

Billy Jordan: There’s a quick checklist. First, make sure your prescriptions are covered under the plan’s formulary. Second, call your doctors and hospitals to confirm they’re in the plan’s network. Third, if you’re delaying Part B because of work, get written proof from your employer about the plan’s creditable status and fill out Form CMS-L564. And finally, think about your travel needs—if you’ll be outside North Carolina a lot, check how your plan covers care when you’re away.

Tanya (AI host): Three things to remember. One, missing your initial Medicare enrollment window can mean penalties that last a lifetime. Two, not all work or retiree coverage lets you safely delay signing up, especially with small employers or COBRA. Three, your choices and timing around Medigap and Medicare Advantage can limit your future options, so know your windows and protections.

Tanya (AI host): For a personalized look at your situation, book a free thirty-minute chat with Billy and his team at thejordaninsuranceagency.com/podcast.

Billy Jordan: I'm Billy Jordan with The Jordan Insurance Agency. Until next time, take care.

Tanya (AI host): Thanks for listening to Smart Coverage. Real Advice. from The Jordan Insurance Agency.