Mistakes To Avoid During Medicare Open Enrollment with Danielle Roberts

We’re diving into an important topic today—Medicare open enrollment—with none other than Medicare expert and Boomer Benefits co-founder, Danielle Roberts. If you’re familiar with Medicare or navigating it for the first time, this is a blog you don’t want to miss.

Danielle, who also authored 10 Costly Medicare Mistakes You Can’t Afford to Make, is here to help you steer clear of the common pitfalls during this crucial time of year.

Medicare Annual Election Period (AEP)

Runs from October 15th to December 7th each year. During this time is your chance to enroll in, change, or disenroll from a Medicare Advantage plan or a Part D prescription drug plan.

These plans don’t require medical underwriting during this window, which means there are no health questions or pre-existing condition barriers. Because of that, this period is highly regulated to avoid people waiting until they're sick to join, which could skew risk pools and drive costs up for everyone.

Danielle explained how, each fall, Medicare Advantage and drug plans send out an Annual Notice of Change in September. It’s crucial to read that document carefully. Even small changes—like a prescription being dropped from your plan’s formulary—could have a significant impact on your healthcare costs. If everything looks fine, you can let your plan renew. But if something’s off, AEP is your time to act.

And let’s not forget—this is the busiest season of the year for agents like Danielle. As she puts it, “It’s our Super Bowl.” Phone lines are jammed as people scramble to understand benefit changes and make informed decisions before the deadline.

2025 Updates

We also touched on 2025 updates, like the Part B premium, which is set at $185, and the slight bump in the Part A hospital deductible, now $1,776. While many people might think Medicare alone is enough, Danielle emphasized that original Medicare comes with gaps—you pay 20% of outpatient costs out of pocket, and there’s no out-of-pocket maximum like with traditional under-65 insurance. That’s where Medigap (Medicare Supplement) plans or Medicare Advantage plans come in.

Medigap

Speaking of Medigap, these plans are designed to fill those gaps—covering things like deductibles, copays, and extended hospital stays. While more expensive than Advantage plans, they offer greater predictability, fewer restrictions, and national provider access. However, they’re not affected by AEP. If you want to change your Medigap plan, you’ll typically need to undergo medical underwriting, unless you're within your six-month open enrollment window after first enrolling in Medicare Part B.

Medicare Advantage Plans

On the flip side, Medicare Advantage plans often look attractive because of their low or $0 premiums and extra perks like dental, vision, hearing, and gym memberships. But there’s a catch—these plans have networks, and benefits can change each year. Thanks to legislation like the Inflation Reduction Act, which capped drug costs, many Advantage plans are slimming down their formularies or trimming extra benefits to balance out their increased risk.

Danielle emphasized how important it is to review your plan's drug coverage and provider network during AEP. What’s free one year could come with a cost the next.

Medigap or Medicare Advantage

Another point Danielle clarified is that Medigap and Medicare Advantage are mutually exclusive—you have to choose one route or the other.

If you’re someone who values nationwide provider access, no referrals, and more comprehensive coverage, Medigap might be your best bet. But if you’re looking for something lower-cost with built-in extras and don’t mind staying in-network, a Medicare Advantage plan could be right for you.


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Rate Increases

Danielle noted that while they used to rise 5–8% annually, it’s not uncommon now to see increases of 13–15%. You can shop around for a better rate, but outside of the initial enrollment window, you’ll likely face medical underwriting. And while some states like New York, Connecticut, Massachusetts, and Vermont offer year-round open enrollment with no underwriting, the trade-off is significantly higher premiums.

So, what’s the takeaway? Be proactive. Medicare open enrollment is your opportunity to reassess your plan, your health needs, and your costs. Look closely at any notices you receive, and don’t assume your plan is the same as last year. The choices you make now can affect your healthcare and financial well-being for the year ahead.

Cost Differences by State

One thing that surprises many people is how geography plays a big role in Medigap premiums. Danielle mentioned that in Connecticut, Plan G can run as high as $210/month, but that same plan in Dallas-Fort Worth, Texas, could be as low as $100–$120/month for a female turning 65. That’s a huge difference.

Good news

If you move from a high-cost state like Connecticut to a lower-cost one like Texas, your Medigap premium will adjust to the new ZIP code. The coverage doesn’t change, but your price will. Unfortunately, the reverse is also true—moving from a low-cost state to a high-cost one will increase your premium. So while your Medigap coverage travels with you, your rate doesn’t lock in nationally.

Drug Plans (Part D)

Danielle also emphasized the importance of choosing a robust Part D drug plan. While some plans may offer $0 or $5 premiums, they often have higher deductibles, fewer covered drugs, and bigger copays. She typically recommends plans in the $40–$60/month range to ensure good formulary coverage, especially for unexpected medications.

Big update for 2025: The out-of-pocket max on drug costs drops from $8,000 to $2,000 due to the Inflation Reduction Act—a major help for anyone on brand-name or specialty meds.

Picking the Right Broker

Choosing the right Medicare path is a big deal—and doing it alone is tough. Danielle pointed out that working with a broker like Boomer Benefits is free, since they’re paid by the insurers. But not all brokers are created equal. Look for:

  • Independence – Do they represent multiple companies?

  • Support – What kind of back-end help do they offer when issues arise?

Boomer Benefits, for instance, has a 75-person client service team dedicated to helping policyholders navigate denied claims, billing errors, appeals, and late penalties. Danielle shared that since 2021, their team has saved clients over $3 million by resolving billing issues they didn’t actually owe. If you enroll directly through an insurer, you're on your own.

Final Advice from Danielle

“If you’re turning 65 in the next couple years, start your research now,” Danielle says. Read books, attend webinars, watch YouTube videos, and familiarize yourself with medicare.gov. The earlier you understand your options, the better your decision will be—and the less stressful it will feel.

Peace of mind through trusted advice - Check out this week’s episode on: 8 Ways to Minimize Your RMDs

If you have a question or topic that you’d like to have considered for a future episode/blog post, you can request it by going to www.retirewithryan.com and clicking on ask a question. 

As always, have a great day, a better week, and I look forward to talking with you on the next blog post, podcast, YouTube video, or wherever we have the pleasure of connecting!


Written by Ryan Morrissey

Founder & CEO of Morrissey Wealth Management

Host of the Retire with Ryan Podcast

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