Medicare Enrollment Checklist for Caregivers

Before You Start: Get Legal Authority

Most caregivers discover this too late—you cannot call Medicare on your parent's behalf, access their claims, or manage enrollment decisions without formal authorization. Before touching any plan comparison, secure these documents:

• CMS-10106 (Authorization to Disclose Personal Health Information): lets Medicare share your parent's records with you. Without it, the 1-800-MEDICARE line can't even confirm what plan they're on.
• Healthcare Power of Attorney: authorizes you to make medical decisions if your parent can't.
• Durable Financial Power of Attorney: lets you pay premiums, manage bank accounts, and handle Medicaid applications.
• HIPAA Authorization: permits doctors and hospitals to share medical records with you directly.

Get these signed while your parent can still consent. If cognitive decline has already set in, you may need guardianship proceedings, which are slower and far more expensive.

The Enrollment Timeline

Your parent's Initial Enrollment Period (IEP) is a seven-month window: three months before the month they turn 65, the birthday month itself, and three months after. Missing this window triggers a 10% Part B premium penalty for each full 12-month period they could have enrolled but didn't—and that penalty lasts for life.

If your parent is still working with employer health coverage, they can delay Part B without penalty. But the Special Enrollment Period after employment ends is only eight months. Start the paperwork 60–90 days before the last day of employer coverage to avoid a gap.

Key deadlines to track:

• Part A enrollment (hospital): automatic if your parent is receiving Social Security; otherwise file during the IEP
• Part B enrollment (medical): must actively enroll during IEP or within eight months of leaving employer coverage
• Medigap Open Enrollment: six months starting the first month your parent is both 65+ and enrolled in Part B—this is the only guaranteed-issue window in most states
• Part D (prescription drugs): enroll during the IEP or within 63 days of losing other creditable drug coverage

Documents to Gather

Pull these together before sitting down with a SHIP counselor or starting online enrollment:

Identity and eligibility:

• Social Security card or SSA-1099
• Medicare card (if Part A is already active)
• Proof of citizenship or lawful residency
• Form CMS-L564 (Request for Employment Information) if delaying enrollment due to employer coverage—your parent's employer completes this

Health information:

• Current medication list with dosages and prescribing doctors
• List of all current physicians, specialists, and preferred hospitals
• Recent diagnoses and ongoing treatments
• Any planned surgeries or procedures in the next 12 months

Financial:

• Most recent tax return (two years prior)—determines whether IRMAA surcharges apply to Part B and Part D premiums
• Current employer health plan summary, if applicable
• Pension or retirement benefit documentation

The Coverage Decision

With documents in hand, the next step is choosing between Medicare Advantage and Original Medicare + Medigap. The choice depends on your parent's health trajectory, provider needs, and risk tolerance.

Run the numbers for both paths: Medigap Plan G premiums plus Part D premiums versus Medicare Advantage premiums plus estimated copays based on your parent's expected care use. The comparison that matters is worst-case annual cost, not the premium line alone.

Check every provider on your parent's care team against the Medicare Advantage plan's directory—then call each office directly to confirm. Provider directory errors are common enough that CMS has investigated them repeatedly.

After Enrollment

Within the first month of coverage, verify:

• All providers accepted the new plan (call offices, don't rely on directories)
• Prescriptions transferred and are on the plan's formulary
• The Medicare Prescription Payment Plan is set up if your parent's monthly drug costs are high (it spreads covered Part D out-of-pocket costs into monthly installments at no extra cost, up to the annual $2,100 cap)
• Your authorization documents (CMS-10106, POA) are on file with Medicare, your parent's primary care physician, and their pharmacy

Our Medigap vs Medicare Advantage guide includes the complete enrollment timeline with penalty calculations, a cost comparison worksheet, and legal authority templates to get your family set up before the first deadline hits.

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