Medicare, one question at a time.

These are the questions we answer at every Desert65 Medicare 101, in the order we teach them. Read straight through, or jump to the one that has been on your mind. Every answer comes with the same picture we put on the screen.

Come to a free Medicare 101 Start reading

Medicare Mary — she talks to a licensed agent before she decides anything, and she sleeps great.

Who should I listen to?

Everybody turning 65 meets two kinds of people. Medicare Mary talks to a licensed agent before she decides anything. Neighbor Ned gets his advice from his brother-in-law, Facebook and Google — and he is very confident. Whenever Ned shows up in this story, something is about to go wrong.

Timing is the first place it shows. Procrastinating Pete turns 65 in September and files the Medicare envelope with the Costco coupons. Early Bird Ernie turns 65 in October and calls in July. October arrives and Ernie has nothing to scramble for.

Neighbor Ned gets his Medicare advice from his brother-in-law, Facebook and Google — and he is very confident.

Procrastinating Pete turns 65 in September and files the Medicare envelope with the Costco coupons; in November he learns timing matters.

Early Bird Ernie turns 65 in October and calls in July, so October arrives with nothing to scramble for. — Be an Early Bird Ernie, not a Procrastinating Pete.

When do I need to sign up?

Your first chance is a seven-month window: the three months before your 65th birthday month, your birthday month, and the three months after. Sign up early in that window and Medicare starts the month you turn 65.

What if I miss my window?

Missing it is not the end of the world, but it costs you. You may wait months for coverage to start, pay a Part B premium that is 10% higher for every 12 months you were late — for as long as you have Medicare — and pay a Part D penalty if you go 63 or more days without drug coverage.

Know your dates. Your Initial Enrollment Period comes once.
Don't delay. The longer you wait, the more it can cost.
Talk with an agent about your options. Peace of mind today, lower costs tomorrow.

What can happen if you miss your window: wait longer, higher Part B costs, a Part D penalty, and not being able to use Medicare as coverage yet. Easy to avoid: know your dates, don't delay, talk with an agent.

Am I enrolled automatically?

One question changes all the instructions: are you already receiving Social Security? Automatic Annie is. Her red, white and blue card shows up about three months before her birthday and she does nothing. Manual Marvin is the same age with the same birthday month, but he is not on Social Security yet — so nothing shows up, and he has to apply.

Automatic Annie already collects Social Security, so her red, white and blue Medicare card shows up about three months before her birthday.

Manual Marvin is not on Social Security yet, so nothing shows up and he has to apply for Medicare. — Automatic Annie gets a card. Manual Marvin gets homework.

Marvin's homework is not hard. He can apply online at ssa.gov/medicare, by phone at 1-800-772-1213, or in person at his local Social Security office. The other difference: Annie's Part B premium comes out of her Social Security check; Marvin gets a bill from Medicare, usually every three months.

Marvin's homework: apply online at ssa.gov/medicare, by phone at 1-800-772-1213, or in person at your local Social Security office.

The 2026 Part B premium is $202.90 a month per person — taken out of Annie's Social Security check, billed to Marvin by Medicare every three months. — The Part B premium shown is the 2026 figure. It changes every January.

Still working at 65?

Working Wanda loves her job and has insurance through it. Her neighbor says "take Medicare at 65!" Her coworker says "wait until you retire!" Both sound confident. Neither looked at her plan. The right answer depends on the size of her employer, the coverage from her current job, what each option costs, her spouse's coverage and her prescriptions.

Working Wanda loves her job and has insurance through it; her neighbor and coworker give opposite advice and neither looked at her plan.

Wanda's answer depends on the size of her employer, coverage from her current job, what each option costs, her spouse's coverage and her prescriptions.

The employer's size is the hinge. With 20 or more employees, the work plan pays first and Part B can usually wait with no penalty later. With fewer than 20, Medicare pays first — and if you skip Part B, you can be responsible for 100% of your doctor's costs.

With fewer than 20 employees, Medicare pays first — skip Part B and you can be responsible for 100% of your doctor's costs. — Whatever your situation, it's best to ask an expert.

How does retiring work?

Retirement Randy worked until 68 and delayed Medicare — totally fine. Then he assumed Medicare knew he had retired. Not fine. You have to tell Medicare when you will lose your work coverage and want Part B to start. You get an eight-month special window after work coverage ends, but Medicare does not start the day you ask.

Retirement Randy worked until 68 and delayed Medicare, then assumed Medicare knew he had retired.

The rule: tell Medicare when you will lose coverage and want Part B to start. You get an eight-month special window after work coverage ends, but Medicare does not start the day you ask.

We work backward from your retirement date so your employer coverage and Medicare line up — no gaps in coverage.

What if I'm on COBRA?

COBRA Carl retires at 65. HR says "you get COBRA for 18 months," and Carl figures he'll deal with Medicare later. Big mistake. COBRA is not coverage from current work, so it does not pause your Part B deadline.

COBRA Carl retires at 65, is told he has COBRA for 18 months, and figures he will deal with Medicare later.

COBRA does not equal coverage from current work, so it does not pause your Part B deadline.

What are Parts A, B, C and D?

Two teams. Parts A and B are run by the government and together they are "Original Medicare": A covers hospital stays, skilled nursing and hospice; B covers doctors, outpatient services, tests and equipment. Parts C and D come from private companies: C is Medicare Advantage, private plans that bundle A, B and usually D; D is prescription drug coverage.

Run by the government: Part A for hospital stays, skilled nursing and hospice, and Part B for doctors, outpatient services, tests and equipment — together, Original Medicare.

From private companies: Part C, Medicare Advantage plans that bundle A, B and usually D, and Part D, prescription drug coverage.

Supplement or Advantage?

Think of it like two resort styles. All-Inclusive Al picks a Medicare Supplement: he pays a monthly premium and most of his Medicare-covered costs are already handled when he needs care. Pay-as-you-go Patty picks a $0-premium Medicare Advantage plan: low cost up front, then copays or coinsurance for visits, hospital stays and tests as she uses them. Neither one is better for everyone. One of them is better for you.

All-Inclusive Al chooses a Medicare Supplement and pays a monthly premium, so most of his Medicare-covered costs are already handled when he needs care.

Pay-as-you-go Patty chooses a $0-premium Medicare Advantage plan — low cost up front, then copays as she uses services.

The Supplement is the all-inclusive stay: hospital, skilled nursing, hospice and any doctor that takes Medicare, anywhere in the country — but Part D, dental, vision, hearing, gym and over-the-counter items are not included. Medicare Advantage often has a $0 premium (you still pay Part B), uses a plan network, charges you for what you use up to a yearly limit, usually builds in drug coverage, and often adds the extras.

Supplement, the all-inclusive resort: hospital stays, skilled nursing, hospice and any doctor that takes Medicare are covered.

Medicare Advantage, Part C: $0 monthly premiums are common, a plan network, you pay for what you use up to a yearly limit, drug coverage usually built in, and extras often included.

Not included with a Supplement: Part D, dental, vision, hearing, gym membership and over-the-counter items.

Will my doctor take it?

Doctor-Loyal Diane only cares about one thing: is Dr. Smith in the network? Great — then we only look at plans that include Dr. Smith. Before you pick any plan, check your primary doctor, every specialist you see, your hospital, and anywhere you travel or snowbird. The coolest commercial is useless without Dr. Smith.

Doctor-Loyal Diane only cares whether Dr. Smith is in the network — so we only look at plans that include Dr. Smith.

Before you pick a plan, check your primary doctor, every specialist you see, your hospital, and anywhere you travel or snowbird.

We don't start with a specific insurance company. We start with you.

Are my prescriptions covered?

Prescription Patty takes 15 medications. Her neighbor loves their plan, so Patty wants the same one. Great plan for the neighbor — terrible fit for Patty. Plans differ on which drugs are covered, what tier each drug sits in, and which pharmacies are preferred. Same zip code, same age, different medicine cabinet. Check first.

Prescription Patty takes 15 medications and wants her neighbor's plan — a great plan for the neighbor and a terrible fit for Patty.

Plans vary on which drugs are covered, what tier each drug is in, and which pharmacies are preferred.

Same zip code, same age, different medicine cabinet. Check first.

Is the $0 plan the best?

Zero-Dollar Zeke found the cheapest plan — $0 premium! He found the premium. He has not found the cost yet. Every plan has several costs: the premium, copays, the maximum out-of-pocket, prescriptions, and the doctor network. The premium is one part of the big picture.

Zero-Dollar Zeke found the cheapest plan — a $0 premium. He found the premium; he has not found the cost yet.

Every plan has several costs: the premium, copays, the maximum out-of-pocket, prescriptions and the doctor network.

When can I change plans?

Three windows. October 15 – December 7 is Annual Enrollment, when everyone can change plans for the new year. January 1 – March 31 is the Advantage Open Enrollment window: if you are on an Advantage plan, you get one switch. And any time you qualify for a Special Enrollment Period — you move, lose coverage, qualify for Extra Help, and more. Supplement plans can be changed at any time, but the new company may ask health questions.

Should I review it every year?

Set-It-and-Forget-It Fred picked a plan four years ago and hasn't looked since. "It worked fine last year." Since then his prescriptions changed, one doctor left the network, the plan changed its benefits, and a letter came every fall. Fred didn't change. Everything around Fred did.

Since Fred last looked: his prescriptions changed, one doctor left the network, the plan changed its benefits, and a plan letter came every fall.

An annual review finds changes before they become surprises. Watch for your plan's ANOC letter every September.

Neighbor Ned's greatest hits

"Wanda, you don't need Part B." "Patty, all the drug plans are pretty much the same." "Zeke, $0 means free." "I picked my plan because Joe Namath was on TV." Ned is a nice guy. He's just not a Medicare expert.

Ned told Wanda she didn't need Part B — but he never looked at her options.

How do I do this right?

Be a Medicare Mary. Borrow her five-step checklist.

Know your dates. Build the timeline early.
Check every doctor. Before you pick a plan.
Answer the Social Security question. Automatic, or homework?
Run every prescription. Same plan ≠ same fit.
Review every year. Before surprises find you.

A Retirement Ready Roadmap: confirm your Part A status, check how Medicare works with your employer plan, mark your coverage-change date, apply for Part B, complete a full review, schedule your plan-selection appointment, enroll, and confirm your card arrived.

Make sure to talk with an agent before you check a box or delay Part B — it could be a very costly mistake. — Mary does this with her agent. It takes about 45 minutes and costs nothing.

What does a review look like?

About 45 minutes, by phone or in person. No cost, no obligation — talking with us is always free. We are independent, so we compare plans from many companies. We start with you: your doctors, your drugs, your budget. And we check it again every year before it changes.

What a review looks like: 45 minutes by phone or in person; no cost, no obligation; independent, comparing plans from many companies; we start with you — your doctors, drugs and budget; and we review it every year.

A word about AI

We use it, but differently than most companies. AI does the busy work behind the scenes — organizing, comparing, analyzing, researching — so nothing gets missed. That frees us up for the important things: talking to you, helping solve problems, and answering your calls. Technology behind the scenes. People in front of you.

Have a question that isn't here?

Bring it to a Medicare 101, or skip the room and just call. About 45 minutes, no cost, no obligation — and we start with you, not the insurance company.

See upcoming Medicare 101s Call (928) 900-0277