My Medicare confession

Oh boy, where do I even start? After 18 years penning this column, sharing tips and tales to help you navigate the golden years, I’ve got a confession that’s got me eating a hefty slice of humble pie—washed down with a chaser of embarrassment. Yep, yours truly got slapped with Medicare’s Late Enrollment Penalty (LEP).

Me! The guy who’s been preaching about timely planning since before smartphones were a thing. If I had a nickel for every time I’ve advised folks to dot their i’s and cross their t’s with Medicare, I’d be retired on a beach somewhere. Instead, here I am, paying extra every month because I thought I knew better. Lesson learned!

So, let’s dive into this LEP beast—what it is, where it came from, what sets it off, and how you can dodge it like a pro.  

First off, what exactly is this LEP that turned my wallet into a cautionary tale? The Late Enrollment Penalty is Medicare’s way of adding a financial sting to your premiums if you don’t sign up for certain parts of the program when you’re first eligible. It’s not a slap on the wrist; it’s more like a perpetual pinch in your pocketbook.

Specifically, it hits Parts B (doctor visits, outpatient care, and preventive services) and D (prescription drugs). Part A (hospital stays) has its own version, but it’s rarer since most folks get it premium-free after working long enough. Think of the LEP as Medicare’s polite (but firm) reminder: “Hey, join the party on time, or pay extra for the late fee—forever.”

Now, let’s rewind the clock a bit for some history, because understanding the “why” might make you forgive my blunder (and avoid your own). The LEP for Part B dates back to the very birth of Medicare in 1965, when President Lyndon B. Johnson signed it into law as part of the Social Security Amendments. Back then, lawmakers were worried about “adverse selection”—a fancy term for people only signing up when they’re sick, which would jack up costs for everyone.

So, they baked in this penalty to encourage prompt enrollment, ensuring a balanced pool of healthy and not-so-healthy folks to keep premiums stable. It was a smart move for the program’s longevity, but boy, does it sting when it bites you!

Fast forward to 2003, when Congress passed the Medicare Prescription Drug, Improvement, and Modernization Act, introducing Part D in 2006. Same logic applied: without a nudge to enroll early, folks might wait until they needed pricey meds, skewing the system. The LEP for Part D kicked in right from the start, mirroring Part B’s structure.  

So, what flips the switch on this penalty? It’s all about timing—or lack thereof. For Part B, your Initial Enrollment Period (IEP) is a seven-month window: three months before your 65th birthday month, the month itself, and three months after. Miss that without “creditable coverage” (like solid group health insurance from a job with 20+ employees), and bam—penalty time.

The trigger? Each full year you’re late adds a 10% surcharge to your standard Part B premium (about $185 a month in 2026, give or take). For Part D, it’s sneakier: if you go 63 days or more without creditable drug coverage after becoming Medicare-eligible, you’ll pay 1% of the national average premium (about $34.70 base in recent years) for every month you’re late.

Triggers can include retiring without realizing you need to act fast, assuming your spouse’s plan covers you indefinitely, or—just like me—miscalculating your coverage gaps while juggling work and life.  

Avoiding this pitfall? Easier said than done, but here’s the humble advice from someone who’s living the regret. Enroll during your IEP if you’re not working with creditable coverage—it’s that simple. If you are employed and have good group insurance, you can delay without penalty, but grab a Special Enrollment Period (SEP) when that coverage ends (usually eight months for Part B, two for Part D).

Document everything: get a “creditable coverage” letter from your insurer to prove you weren’t slacking. And don’t forget Open Enrollment for Part D (October 15 to December 7) if you need to switch plans. If life’s thrown you a curveball—like misinformation or a qualifying event—appeal the penalty through Social Security. Trust me, prevention is worth a pound of cure; I wish I’d double-checked with a SHIP counselor (that’s State Health Insurance Assistance Program—free and fantastic in Georgia at 1-866-552-4464).

But here’s the kicker that really stings, and I can’t emphasize it enough: the LEP isn’t a one-and-done fine. Oh no, it’s a permanent monthly add-on for the rest of your life! For me, that means shelling out extra bucks every single month until… well, forever. It’s like subscribing to a magazine you never wanted, but Medicare’s the editor who won’t let you cancel.

If you’re late by two years on Part B, that’s a 20% hike—potentially $37 more monthly in 2026 premiums—tacked on indefinitely. Part D? A year’s delay could mean $4 extra a month, compounding over decades.  

Fellow seniors, don’t let my embarrassment be in vain. The LEP is a relic of good intentions from 1965, but in today’s world of longer lives and complex retirements, it’s a trap even “experts” like me can fall into. Check your enrollment status, chat with Medicare.gov or call 1-800-MEDICARE, and lean on local resources here in Georgia.

Life’s too short for lifelong penalties—learn from my humble pie, and keep your wallet happy. Until next time, stay enrolled and stay sharp!

Thanks for reading All About Seniors. See you next week!

Bill Milby is a Director of Visiting Angels® of Central Georgia, a non-medical, living assistance service for seniors. If you have questions or comments about this column, you can reach him at william.mercylink@gmail.com or search for us at  facebook.com/VisitingAngelsofCentralGA.