Corey Romero, Medicare Insurance Broker

Medicare, Medications & Mistakes: Avoiding Costly Underwriting Surprises

March 10, 2025

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What is the biggest mistake seniors make when enrolling in Medicare?

Answer: The biggest mistake I see seniors make when enrolling in Medicare? Pretty simple. They listen to commercials with retired athletes or actors instead of getting real advice from someone they actually trust.

They pick a plan because it says “$0 premium” or “extra benefits,” but don’t realize what they’re giving up until it’s too late like higher out-of-pocket costs, network restrictions, or a drug plan that doesn’t even cover their meds.

Medicare isn’t hard when you’ve got someone who sees you as a person, not a policy number or commission check. It feels like a pain because it’s designed that way so you’ll make a fast decision and never look back.

The key? Honest, no-pressure guidance from someone who knows the system and gives a damn. Not the people on TV reading a script about a “great” Medicare plan he probably doesn’t even use because, let’s be real, they’re either not on Medicare or have a low-cost group plan.

Start with a conversation, not a commercial.

Can you describe a time when you helped a client navigate a complex Medicare issue?

Answer: Sure! Here’s a recent one that sticks with me:

I had a someone call in who was transitioning from employer coverage to Medicare, but she was still working part-time and had COBRA offered to her. The HR department gave her some half-baked advice and basically told her to take COBRA and “figure out Medicare later.” Problem is, that can screw up your Medicare Part B enrollment and lead to a lifetime penalty or delayed coverage start.

When she reached out to me, she had no idea that COBRA doesn’t count as creditable coverage for delaying Medicare enrollment. If she followed their advice, she would’ve ended up paying more forever and had a gap in her health insurance.

I walked her through exactly how to enroll in Part B on time avoiding those penalties and helped her choose a supplement that kept her doctors and medications covered without all the network drama that she had faced on her group plan.

Her exact words after we finished: “Why didn’t anyone tell me this earlier?”

My answer? “Because they don’t get paid to.”

The unfortunate truth is that HR employee likely didn’t have bad intentions but was simply going off of the limited knowledge that they had so it is a great example of why it’s so important to work with someone who really knows the intricacies of Medicare enrollment.

This is what we a great agent will do. We cut through the noise and get people the right coverage the first time. No guessing. No confusion. Just the truth.

I’ve been on a Part D plan for a while, and I’m wondering why my generic prescriptions suddenly cost more. Did something change?

Answer: If your same prescriptions from the same pharmacy on the same drug plan suddenly cost more this year, you’re not crazy. Part D plans reset every January, and even if you didn’t switch plans during Annual Enrollment Period (October 15 - December 7), your plan may have changed on you!

The drug list, or formulary, may have shifted, bumping your med to a higher tier with a higher copay or dropping it from coverage altogether. They send those notices out in easy to overlook mailings and e-mail notifications that are generally ignored by many people who are happy with their coverage. That is, until those changes take effect.

And we can’t forget about the pharmacy game. If your go-to mom and pop shop isn’t considered a “preferred” pharmacy anymore, you’ll end up paying more just for sticking with what’s familiar. The big boys are playing hard ball and sometimes our local pharmacies end up paying the price or are forced to pass that on to you.

Bottom line: plans change, prices go up, and most people don’t find out until they’re standing at the pharmacy counter in January.

Don't wait to review these changes after you receive the shocking bill. Stay on top of changes or work with someone who will help review your options as part of your client relationship.

I've heard about IRMAA affecting my Medicare premiums. How can I find out if it applies to me, and how does it work?

Answer: IRMAA is always (NOT) a fun surprise and many folks don’t see it coming. It stands for Income-Related Monthly Adjustment Amount, but really, it just means Medicare is charging you more because you “made too much” two years ago. Yay, right?

Medicare looks at your income from two years back - so in 2025, they’re using your 2023 tax return. If your income was over a certain amount, you’ll pay extra for Part B and Part D. And no, it’s not always a small bump - it can be a few hundred bucks more per month depending on your income level.

You’ll get a letter from Social Security if IRMAA applies. The timing of that letter? Let’s just say it's government issued and doesn’t always conveniently show up BEFORE you’ve already picked your plans and thought you had your costs locked in.

If you’re not working with someone who brings this up ahead of time, that Social Security letter is not a fun one to open. That’s why it helps to trust your advisor who’s actually looking ahead - not just plugging in plan info or letting you go at it alone.

The good news? If your income has gone down if you just retired, sold a business, or lost a spouse - you can appeal it using form SSA-44 to get those premiums adjusted.

If your 2023 income was over $103,000 (single) or $206,000 (married filing jointly), it’s worth looking into. If not, you’re probably good. Either way, the key is catching it before you’re stuck wondering why your Medicare bill just jumped.