Summary. Five sequences — enrollment, plan choice, annual review, service-termination appeals, and claim appeals — each item with its governing deadline.

1. Six to nine months before 65

  • Confirm the exact Initial Enrollment Period dates: three months before the birthday month, the birthday month, three months after.
  • Answer the threshold question: will there be coverage through current employment at 65?
  • If yes, determine the employer's size. Twenty or more employees: group plan primary, Part B may be delayed. Fewer than twenty: Medicare primary — enroll in Part B.
  • Get the employer's answer in writing from human resources.
  • Confirm whether retiree coverage or COBRA is involved. Neither is current-employment coverage. Neither supports a Special Enrollment Period.
  • Ask whether prescription coverage is creditable — get the annual creditable coverage notice and keep it.
  • If contributing to a health savings account, stop contributions six months before Medicare enrollment (Part A can be retroactive six months).
  • Decide on Part A: take it if premium-free and no HSA contributions; delay if still contributing to an HSA.
  • Calendar the enrollment window with a reminder 30 days before it opens.

2. Enrolling

  • If already receiving Social Security, confirm automatic Parts A and B enrollment and the card's arrival.
  • If declining Part B because of qualifying employer coverage, follow the decline instructions exactly and keep proof.
  • Otherwise apply through Social Security — online, phone, or in person — in the three months before the birthday month.
  • For a Special Enrollment Period, obtain the employer-completed verification form before leaving the job.
  • Calendar the eight-month Part B window from the end of employment or coverage, whichever is first.
  • Calendar the 63-day Part D window from the end of creditable drug coverage.
  • Confirm the effective date in writing before relying on it.
  • Photograph the Medicare card; store the number securely.

3. Choosing a path — the six-month Medigap window

  • Note the window: six months from the first month both 65 and enrolled in Part B. It closes once.
  • Check whether your state requires continuous or annual guaranteed issue — a few do, which makes the choice reversible.
  • Decide between original Medicare with a supplement and Medicare Advantage:
    • Specialist relationships to preserve?
    • Two states, or extensive travel?
    • Serious chronic condition?
    • Is the supplement premium genuinely affordable?
    • Are all providers in one local network?
    • Is avoiding prior authorization important?
  • Note the asymmetry: original + supplement stays reversible; Advantage may not, except during the 12-month trial right.
  • If choosing original Medicare: compare Medigap plans by letter (benefits are standardized), on price, rate-increase history, and rating method.
  • Buy the supplement inside the window.
  • Enroll in a standalone Part D plan the same week.
  • If choosing Advantage: verify the network by calling each provider's office; verify the formulary drug by drug; note the out-of-pocket maximum.
  • Calendar the 12-month trial right end date.

4. The annual review — 15 October to 7 December

  • Read the Annual Notice of Change received in September.
  • List every medication with dosage.
  • Check each drug against next year's formulary: covered? tier? prior authorization? step therapy?
  • List every provider by name.
  • Check each against next year's network — and call each office to confirm.
  • Run the plan finder with the actual drug list.
  • Compare total expected cost: premium + deductible + copays + bad-year out-of-pocket maximum.
  • Check star ratings and complaint data.
  • Re-screen for Extra Help and a Medicare Savings Program.
  • Make the change by 7 December, or confirm the decision to stay.
  • In January: confirm the new card, the pharmacy's records, and the first fill.

5. On hospital admission

  • Ask on day one: "Am I an inpatient or under observation?" Ask again daily.
  • Get the answer in writing; read the observation notice.
  • If observation and the clinical picture supports admission, ask the attending physician to reconsider while still in the hospital.
  • Before any transfer to a skilled nursing facility, confirm the three-day inpatient stay exists.
  • Ask the case manager to document the qualifying stay.
  • Keep the Important Message from Medicare given at admission and again before discharge.

6. When services are ending — the two-day clock

  • Read the Notice of Medicare Non-Coverage or the Important Message from Medicare.
  • Find the Quality Improvement Organization phone number on the notice.
  • Call it immediately — by noon the day before the stated end date. Services continue during review.
  • Ask the provider for the detailed notice explaining the reason.
  • Ask the treating physician for a statement supporting continued need.
  • Do not accept "the patient has plateaued" — maintenance care can qualify.
  • If the provider says Medicare will not pay, request a demand bill so Medicare makes the determination.
  • Note the decision date; if adverse, proceed to the next level.

7. Appealing a claim denial — original Medicare

  • Read the Medicare Summary Notice; identify claim number, date of service, provider, denial code.
  • Level 1 — redetermination: 120 days. File with the contractor.
  • Attach: the treating physician's letter; the records; the applicable coverage rule, national coverage determination, or local coverage determination for your contractor.
  • Level 2 — reconsideration: 180 days. Get all evidence into the file by this stage.
  • Level 3 — ALJ hearing: 60 days. Check the amount in controversy; aggregate claims if needed. Prepare a one-page element outline; have the physician available.
  • Level 4 — Appeals Council: 60 days.
  • Level 5 — federal district court: 60 days, higher amount in controversy.
  • Send everything traceably; log every call with date, name, and reference number.

8. Appealing — Medicare Advantage and Part D

  • Get the denial in writing; a verbal denial is not appealable.
  • Request expedited review whenever delay could harm health — 72 hours standard expedited; 24 hours for an expedited Part D coverage determination.
  • File the plan reconsideration within the stated deadline.
  • Confirm the plan automatically forwarded an adverse reconsideration to the independent review entity.
  • Argue explicitly that the plan may not apply criteria more restrictive than original Medicare.
  • For drugs, choose the right request: formulary exception, tiering exception, prior authorization, or step therapy exception.
  • Ask for the transition fill by name for a new enrollee or a mid-year formulary removal.
  • Get the prescriber's supporting statement — it is required for exceptions.

9. Reducing cost

  • If income dropped due to a life-changing event (work stoppage, marriage, divorce, death of spouse, loss of income-producing property or pension), file an IRMAA redetermination.
  • Apply for a Medicare Savings Program through the state Medicaid agency.
  • Apply for Extra Help through Social Security.
  • Check for a State Pharmaceutical Assistance Program.
  • If QMB-eligible, note that providers may not bill you for Medicare cost sharing — report violations.
  • Ask about the Part D out-of-pocket cap and monthly payment spreading.
  • Have a SHIP counselor screen you for all programs at once.

10. Documents to keep

  • Medicare card and a photo of it.
  • Employer coverage letter and verification form.
  • Evidence of Coverage, formulary, summary of benefits, Annual Notice of Change.
  • Current medication list with dosages.
  • Provider list by name.
  • All notices, in date order, with the next deadline written on the front.
  • A one-page contact sheet: plan member services, SHIP, 1-800-MEDICARE, the state QIO, Social Security.

11. Fraud watch

  • Never give the Medicare number to an unsolicited caller.
  • Refuse "free" equipment, testing, or supplies offered by phone or at the door.
  • Review every Medicare Summary Notice or explanation of benefits for services not received.
  • Report suspected fraud to 1-800-MEDICARE and the state Senior Medicare Patrol.

Related documents

Educational only, not legal advice. Amounts, thresholds, and plan rules change annually; Medigap rights vary by state. SHIP counseling is free.