Which Medicare situation is yours? All eighteen, sorted

Good to be here. So it came together as a kind of master index, eighteen parts of a healthcare-in-retirement series he's been building out, and the whole premise is that Medicare isn't one decision. It's closer to a hundred small ones, and the costly ones are hiding inside completely ordinary moments.

He names three specifically: your last day at work, a letter in the mailbox, and a winter somewhere warm. Which sounds almost poetic, but each one of those can trigger a Medicare deadline or a penalty if you don't know what you're looking at.

October 15 through December 7. So yes, this is not an abstract conversation. People who need to make changes have a window open right now.

Right, and that first situation is one where a lot of people get burned. If you leave a job and go onto COBRA, most people assume the COBRA coverage buys them time on Medicare enrollment. It does not.

Medicare does not treat COBRA as job coverage. So that eight-month window to sign up for Part B starts the month after your job ends, not when COBRA runs out. If you wait for COBRA to expire, you could be enrolling late.

A permanent one. That's not a typo. It doesn't go away after a few years. It follows you.

And the COBRA situation is not the only wrinkle at retirement. If you're 65 and still working, with a spouse on your employer plan who's younger, there's real math to do. Ian walks through whether you keep the family plan or move yourself to Medicare, and it includes this income-related surcharge called IRMAA.

So Medicare's standard Part B premium, the baseline, is $202.90 a month in 2026. But if your income is above certain thresholds, Medicare adds a surcharge on top of that. And here's the kicker: they're not looking at what you made this year. They're looking at your tax return from two years earlier.

Exactly. A lot of people retire, their income drops, and they still get hit with IRMAA for a year or two because of prior income. There are ways to appeal it if your situation has genuinely changed, but our advisors know the specifics of that process much better than I'd want to summarize here. That's a great question to bring to them.

If you're still contributing to an HSA and you sign up for Medicare, even just Part A, you have to stop contributing. If you don't, you've made excess contributions, and the tax consequences are not pleasant.

That's the rule. And Ian flags it because people who love their HSAs sometimes delay enrollment specifically to keep contributing, which is a legitimate strategy, but it has its own timing considerations. The details there are really worth a direct conversation with one of our advisors.

This one surprises almost everyone. If your company has fewer than 20 employees, Medicare generally pays first, not your work plan. So if you're 65, working at a small company, and you haven't signed up for Part B, you could be getting bills that your work plan has no obligation to cover.

Right. The plan designed itself around being secondary. If the primary payer isn't there, nobody's covering that gap.

Ha. Probably more than half. So Medicare Advantage, which a lot of people are on, is built around counties. Your plan covers you in your plan's service area. Leave that area for more than six months, and generally the plan is required to drop you.

You lose that plan. And Ian makes a distinction that matters: visiting somewhere is not the same as moving there. So if you spend summers somewhere else, you're not establishing residency, but you are potentially outside your coverage area for a long stretch.

It has no county line. If a provider accepts it, you're covered, wherever you are. That's the structural difference.

It can be. And it connects to a point Ian makes throughout the series: the job you're leaving, the letter on the counter, where you spend winter, these can turn out to be one decision instead of three. A planner who sees all eighteen situations at once can spot those connections before they become problems.

It's this trap where you can spend three nights in a hospital bed, you're in a hospital gown, you're getting care, you're being monitored, and technically you are an outpatient.

Because the hospital classified you as under observation rather than admitted. And those three nights, even though you experienced them as a hospital stay, do not count toward the three inpatient days that Original Medicare requires before it covers a skilled nursing facility.

And that bill can be significant. Ian says the facility is required to give you a notice about your status, and he names the one question to ask while you're still in the bed.

Don't wait until discharge. That's the whole point of that section.

This one is worth slowing down on. Medicare Advantage lets you switch plans every fall during Open Enrollment, no health questions, no underwriting. Medicare Supplements, the plans that wrap around Original Medicare, generally do require underwriting if you're not in your initial enrollment window.

That can be very hard. Ian's number is striking: nine in ten enrollees have no guaranteed right to buy a Supplement later. So if you're on that plan, feel fine, and assume you can switch if you ever need more coverage, that assumption might not hold.

That's most people on Advantage. And the door can lock at a moment when you have already become someone who needs a lot of coverage. That's the worst time to find out you can't get a Supplement.

If you're healthy and you don't take any prescriptions, skipping a drug plan feels completely rational. Why pay for something you're not using?

The penalty grows every month you go without coverage. And it's permanent. So the person who skips Part D for five years and then develops a condition where they suddenly need prescriptions is now paying a penalty on top of the premium, sized by those five years, for as long as they have Medicare drug coverage.

I didn't put it together. I'm just reporting on it.

Two letters that can show up and look similar. One says your plan is changing for next year. The other says your plan is going away. And they are not the same thing.

Right. Ian's piece on that, which is part six, shows specifically how to tell the two apart. Part seven goes deeper and reads the Annual Notice of Change like a spec sheet, including two cost measurements that people routinely confuse. And part eighteen is fascinating because it shows how to use an AI assistant to help read the same letter.

Ian is very direct about this: Medicare says it will never call to sell you anything. Federal rules bar cold calls from plans and agents who don't already have your permission. So if a call comes in during Open Enrollment from someone saying they're with Medicare and they have a plan for you, that call is not what it claims to be.

He does. I'd say read part seventeen for those, because they're worth having ready.

Part fourteen might be the one to bookmark, because it lists seven things no AI can know about your Medicare. Because they're not public yet, or they're public only county by county or state by state, or they exist only in your own file.

Exactly. And part eighteen shows five prompts to type in order when reading your Annual Notice of Change with an AI, plus what not to paste in, and the three questions the assistant simply cannot answer from that letter. It's a very practical framework.

It's a federal pilot program that now reviews prior authorization requests for a specific list of services in Original Medicare in six states, and Arizona is one of them. The rules require that a human clinician review every denial. Ian covers what to do if a request stalls.

Part fifteen is the one to read for that.

Two important ones. For veterans with VA care, the VA and Medicare don't coordinate. Outside the VA system, you're on Original Medicare, and Original Medicare Part B pays 80 percent of covered services with no cap on what you could owe in a year. Part three covers how an Advantage plan can add a yearly out-of-pocket maximum, though availability varies by county.

It has no premium of its own and covers what Medicare leaves behind. But it requires Part B, and Part B at the 2026 standard rate is $202.90 a month. It also means you generally don't need a separate drug plan, because it handles that.

Right. No cost of its own, but Part B is the bill. That distinction matters when you're budgeting.

That's really what it comes down to. Most of us run into these situations one at a time, usually for the first time, usually in a hurry. A planner has walked families through every single one of them and knows how they connect. All those pieces we were just describing, the ones that feel like separate conversations, they can turn out to be a single decision once somebody's looking at the whole picture.

And Ian's suggestion is straightforward: find your situation in the series, bring that part to the conversation, and start there.

Friday, October 2nd. Two locations. Foothills Library in Glendale at 10:30 in the morning, and Mustang Library in Scottsdale at 2:30 in the afternoon. No cost to attend.

That's the number to call if you want to sit down with a team that sees all eighteen of these situations at once and knows how yours connect.