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Planning checklist

The Medicare checklist we actually walk clients through

It is roughly two dozen small tasks, which sounds heavy until they are sorted into five stages. Worked in order, nothing slips: not a prescription, not a physician, not a deadline.

Figures reviewed for 2026

5
Stages, first to last
6 months
Lead time we recommend
2 lists
Prescriptions and physicians
Once a year
The review that follows

Stage one: build the vocabulary

Expertise is not the goal. Recognition is. You want to notice when a pitch skips past a network, a deductible, or a prior authorization. One focused hour here pays for itself repeatedly.

  • Describe Parts A, B, C and D each in a single sentence, out loud.
  • Lean toward a path: government Medicare plus a supplement, or an Advantage plan.
  • Learn what a Medigap policy will never do, starting with prescriptions.
  • Look at the 2026 amounts so a quoted premium has context.

Stage two: gather what only you know

Those two lists shape your best plan far more than any general rule of thumb. Bring them to every conversation, including ours.

  • Confirm whether Social Security is already paying you, which decides automatic versus manual filing.
  • List every prescription with dose and refill frequency.
  • List your physicians, any specialists, and the hospital you would choose.
  • Note your present coverage and the date it ends, including retiree or COBRA arrangements.
  • Set a premium figure you are comfortable with, plus a separate cushion for copays.

Stage three: file the paperwork

Order beats speed. Part B first, because the supplement window is anchored to it. Drug coverage at the same time, so no month passes bare.

  • Apply for Parts A and B inside your window at ssa.gov or by phone.
  • Pick your path, and apply for the supplement during the six-month protection if you want one.
  • Add a stand-alone drug plan, or verify drug coverage is bundled into your Advantage plan.
  • Record every confirmation number and effective date.

Stage four: switch it all on

One note on overlaps. Paying two premiums for a single month is irritating. A single uncovered month during a health event is worse.

  • Inspect the Medicare card when it arrives and report errors the same day.
  • Open your online Medicare account to follow claims and see preventive coverage.
  • Book the Welcome to Medicare visit within the first twelve months of Part B.
  • End the old coverage so the dates meet instead of overlapping.
  • Decide whether you want dental, vision or hearing coverage alongside.

Stage five: the annual habit

A plan that fit in 2023 may not fit today, and the fall window is the only one that lets you act on Advantage and drug coverage without health questions. We run that comparison for our clients each year and say so plainly when staying put is the right answer.

  • Re-check your Advantage or drug plan each autumn, because formularies and networks move.
  • Book the annual wellness visit, which costs you nothing.
  • Use the screenings before symptoms give you a reason to.
  • Treat any cold call about your Medicare number as fraud, because that is what it is.
  • Re-shop the supplement premium every couple of years if your health allows underwriting.

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Planning checklist

Questions people ask about this

When should I start the checklist?

Six months before the 65th birthday leaves room to confirm dates, gather prescriptions, and compare plans without a deadline forcing a rushed decision.

What if I am already behind?

Most steps can still be done. Inside a window, file now. Outside one, check whether a special period applies, and price out any surcharge before deciding to wait further.

Is the prescription list truly necessary?

Yes. Every plan publishes its own covered-drug list with its own tiers and rules. Without your list, a $10 plan and a $200 plan look identical on paper.

Official sources

Check it at the source

Every figure on this page comes from the agencies below. They are the primary record, and none of these links costs you anything.

Related

Keep reading

Medicare 101The vocabulary to start withTurning 65 timelineDates for each stageDrug coverage stagesHow prescriptions get pricedGet a free quoteHave an agent run your lists against the market

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