Which Medicare situation is yours?

Eighteen parts of Healthcare in Retirement are live, and this is the page to keep. I started the series because Medicare is not one decision. It is a hundred small ones, and the costly ones hide inside ordinary moments: a last day at work, a letter in the mailbox, a winter somewhere warm. Open Enrollment runs October 15 through December 7, so the next few weeks are a good time to find yours. Below is every part so far, sorted by what is happening in your life, with one line on why it matters. Find your situation. Then send the right one to the person who needs it.

Are you still working at 65, or did you just stop?

Three parts. If you are leaving a job with COBRA, part one shows why Medicare does not count COBRA as job coverage, so the eight-month window to sign up for Part B starts the month after the job ends, not when COBRA runs out. If you are 65 and still working with a spouse who is not 65 yet, part two does the arithmetic on keeping the family plan versus moving yourself to Medicare, including IRMAA (the income-related surcharge Medicare adds to Part B and Part D premiums, set by your tax return from two years earlier) and the health savings account rule that can void contributions. And if your employer has fewer than 20 employees, part sixteen explains why the rules flip: Medicare generally pays first, so skipping Part B risks bills the work plan might not pay.

Did you serve?

Two parts, and thank you. Part three is for veterans with VA care: the VA and Medicare do not work together, and outside the VA you are on Original Medicare, where Part B pays 80 percent of covered services with no yearly ceiling on what you could owe. A $0-premium Advantage plan (you still pay the Part B premium, and availability varies by county) can add a yearly cap on what you pay. Part eleven is for military retirees with TRICARE For Life, which has no premium of its own and pays what Medicare leaves behind, but it requires Part B, and Part B is the bill: $202.90 a month at the standard 2026 rate. It also means you do not need a separate drug plan.

Is a letter from your plan on the counter?

Three parts, because September is letter season. Two letters look alike this month, and part six shows how to tell them apart: one says your plan is changing for 2027, the other says it is going away, and the second one carries its own deadlines and rights. Part seven reads the Annual Notice of Change like a spec sheet: how the letter is laid out, the two cost meters people confuse, and what a plan can change mid-year. And part eighteen reads the same letter with an AI assistant: five prompts to type in order, what never to paste, and the three questions no assistant can answer from the letter alone.

Is a Medicare clock running on you?

Three parts on dates that matter more than they look. If you are healthy with no prescriptions, part four shows why skipping a drug plan can still cost you: the late-enrollment penalty is permanent, it grows every month you wait, and the window to fix it opens once a year. If you are on an Advantage plan and think you might want a Medicare Supplement later, part five explains why that door can lock behind you: Advantage plans let you switch every fall with no health questions, Supplements generally do not, and nine in ten Advantage enrollees have no guaranteed right to buy one later. And if the names of the windows blur together, part eight defines every enrollment period with its dates and its source, plus a short path to the one that is yours.

Did a bill surprise you at the pharmacy or the hospital?

Two parts. Part nine explains why the same drug on the same plan can cost more at the pharmacy across the street: preferred pharmacies have agreed to charge less than other pharmacies in your plan's network. It also shows when mail order wins and when it does not. Part ten is the hospital version: you can spend three nights in a hospital bed as an outpatient under observation, and those nights do not count toward the three inpatient days Original Medicare requires before it covers a stay in a skilled nursing facility. It covers the notice the hospital has to give you and the one question to ask while you are still in the bed.

Do you live in two places?

Part twelve is for snowbirds. Medicare Advantage is a county product: leave your plan's service area for more than six months and the rules generally require the plan to drop you, and visiting somewhere is not the same as moving there. Original Medicare has no county line.

Are you using AI, or wondering whether to?

Three parts, from an engineer who uses an assistant every day, plus part eighteen above. Part thirteen is for anyone who tried an AI assistant once and put it down: what has changed since, with dates, and a one-minute test for each complaint. Part fourteen lists seven things no AI can know about your Medicare, because they are not public yet, are public only county by county or state by state, or exist only in your own file. And part fifteen covers WISeR, a federal pilot that now reviews requests for a short list of services in Original Medicare in six states, Arizona among them. The rules say a human clinician must review every denial, and the piece covers what to do if a request stalls.

Did the phone ring?

Part seventeen is for October. Medicare says it will never call to sell you anything, and federal rules bar cold calls from plans and agents who do not have your permission. It covers who is really allowed to call, what the common scams sound like, and the two sentences I say before I hang up.

What a Certified Medicare Planner® does differently

They see all eighteen at once. Most of us meet these situations one at a time, usually for the first time, and often in a hurry. A planner has walked families through every one of them and knows how they connect: the job you are leaving, the letter on the counter, and the county you spend the winter in can turn out to be one decision instead of three. Bring the part that sounds like you, and the conversation starts there. The advisors are at 602-281-3898.

Friday, October 2. Foothills Library, Glendale, 10:30 AM. Mustang Library, Scottsdale, 2:30 PM. No cost. Register at 123easymedicare.com/medicare-workshop or call (877) 220-1089.

This event is presented by 123EasyMedicare, a brand of American Retirement Advisors, an independent, private organization. It is not sponsored by, endorsed by, or affiliated with Medicare, the Centers for Medicare & Medicaid Services, the Social Security Administration, or any government agency. The libraries are not sponsors of, and are not affiliated with, this event. Educational only; not tax, legal, or insurance advice.

Disclaimer: This article is for educational purposes only. It is not sponsored, endorsed, or otherwise representative of Medicare or the federal Medicare program. American Retirement Advisors is not a government agency. For official Medicare information, visit medicare.gov or call 1-800-MEDICARE (1-800-633-4227).