Medicare: Big pitfalls to avoid, part deux

Hey there —

Ermahgerd, Medicare is confusing. Or as John Oliver said in a recent Last Week Tonight segment on Medicare Advantage, “On a scale of one to Inception, it is basically Tenet. And I don’t say that lightly.”

So yeah, like we said in our last Medicare installment, there’s so much important stuff to know before enrolling — and it’s wayyyy more than we can cover in one newsletter.

But luckily, there are resources that can help you wade through the alphabet soup of Medicare’s parts and plans, and we’re going to get into those today.

… and tell you about a deadline you really don’t want to miss.

But first, let’s say it again: Beware the Medicare Advantage hype.

Honestly, you should just watch it.

Oliver’s take: Medicare Advantage is so much worse than traditional Medicare, that it’s misleading to even use “Medicare” in the name.

As examples, he shows reports citing that in the majority of Medicare Advantage plans, 30 to 60 percent of the locations in their provider directories are inaccurate, and that virtually 99% of Medicare Advantage enrollees are required to obtain prior authorizations for some services.

And he takes particular aim at the industry’s relentless and often misleading marketing tactics — like celebrity-studded commercials that flood cable TV.

“Whatever you do, do not call those broker numbers on TV, because they won’t give you unbiased advice. They get much higher commissions if they funnel you to Advantage plans,” he says. Point taken.

Luckily, there are trustworthy resources out there.

As we mentioned in our last installment, every state has an agency called SHIP (for State Health Insurance Assistance Programs) you can call to help you navigate all this.

And there’s the Medicare Rights Center — they help over 20,000 folks a year with this stuff.

And the big takeaway from our reporting last year: You should definitely call one of these places when it’s getting close to your 65th birthday. Because you have a limited window to enroll in Medicare: three-and-a-half months on either side of your 65th birthday.

Even if you’re leaning toward a Medicare Advantage plan (despite John Oliver’s warnings), you still gotta do this.

So figure out when that is, and save the dates in your calendar.

Seriously, don’t blow that deadline.

If you miss it, you can still sign up eventually… but you have to pay a penalty every year for the rest of your life.

And millions of folks end up paying Medicare late-enrollment penalties each month because they missed enrollment deadlines, according to an AARP report.

There are some exceptions to this rule where you can avoid that penalty — like if you’re still working after 65 and have insurance through your job.

But figuring out whether you qualify for an exemption — and finding the right paperwork to submit if you do — can be super confusing. And finding a straight answer online is nearly impossible. (At least it was for me. And my editor. And Dan.)

So again: Get help from a human. Reach out to the folks at SHIP or the Medicare Rights Center to walk you through it. Seriously, save those links.

And if you haven’t been convinced yet, you’re about to be. Because it’s time to dive into the alphabet soup of Medicare’s parts.

A, B, C, Easy as…

Hahahaha we wish. Of course, it’s complicated.

You might have heard the terms Medicare Parts A, B, and C. Part C, confusingly, is Medicare Advantage, so let’s put that aside for now.

Part A covers inpatient care — hospitals, skilled nursing facilities, and hospice.

Part B pays 80% of your doctor’s visits and related care, like tests, as well as medical supplies and preventive services. Everyone pays a monthly premium for Part B, usually deducted from your social security check. (In 2026, that’s estimated to be $206.50.)

And yep, by everyone, we also mean folks on Medicare Advantage plans, too.

Some Advantage plans promise “$0 premiums.” But Emily Whicheloe, director of education at the Medicare Rights Center, calls those claims “misleading,” and says it’s one of the top things they get questions about.

“A $0 premium does not mean you are off the hook for the Part B premium,” she says. “Everyone is responsible for that, even if you take a Medicare Advantage plan.”

So yeah, cue John Oliver slamming on his desk.

There are more letters!

Head already spinning?

First there’s Part D, drug coverage — all of which is administered by for-profit companies. It’s a whole thing we’ll get into in future installments.

Then there are the supplementals — AKA Medigap plans — to fill in that “gap” of 20% not covered by Part B in traditional Medicare, as well as other copays, deductibles, and co-insurance.

And for the supplementals…the whole alphabet starts over again! Medigap includes plans labeled A, B, C, D, F, G, K, L, M and N.

Here’s a chart that summarizes what each Medigap option generally covers. But once again, it’s probably better to bring in the experts to help you navigate this alphabet soup.

So one more time:

SHIP: https://www.shiphelp.org/ 

Medicare Rights Center national helpline: 800-333-1144

The feds also run a 1-800-Medicare phone line you can call with questions (though that may be less helpful until the end of our government shutdown.)

And if you want a deep dive: Check out journalist Phil Moeller’s book Get What’s Yours for Medicare. He has done his homework. Or follow his Substack “Aging in America.”

And another great resource is the book Medicare for You by Diane Omdahl. We spoke with both Diane and Phil while putting together this newsletter series.

And a final word of caution: As Oliver’s segment highlights, as you approach 65, you’ll probably get calls from insurance brokers, or be invited to “understanding Medicare” workshops. Brokers can be helpful, but as this study underlines, many brokers have a financial incentive to steer you to Medicare Advantage. So stay on guard.

Whew, that was scary. At least… It’s a great transition to a spooky weekend?

Have a Happy Halloween — and let us know if you have any health-care-inspired costumes you’re rocking this fright night. Like, anyone out there dressing up as an insurance denial.

— Claire