Quick answer. Medicare's initial enrollment period runs seven months: three months before your 65th birthday month, the month itself and three months after. Sign up in the first three months for coverage that starts in your birthday month. Then update your power of attorney, health care directive, will and beneficiary forms.
The Medicare window
According to the Washington State Office of the Insurance Commissioner's Medicare page (source):
- The initial enrollment period is seven months around your 65th birthday, from three months before your birthday month to three months after.
- Sign up in the three months before your birthday month and coverage starts the first day of that month. Sign up during it or after and coverage starts the first day of the next month.
- Miss it, without a special enrollment period, and the general enrollment period is January 1 to March 31, with coverage starting the month after and a possible late penalty.
If you're still working with employer coverage, ask your plan administrator before deciding not to enroll. Once you're on a drug plan, our Part D out-of-pocket cap tracker helps you watch spending.
Social Security is a separate decision
You can sign up for Medicare without claiming Social Security. The claiming age comparison shows what waiting does to the monthly amount.
The documents your family would need
- A durable power of attorney for money and property. See power of attorney requirements by state.
- A health care directive naming who decides if you can't. See living wills and health care proxies.
- A current will, and beneficiary forms on retirement accounts and life insurance that match it.
- A list of accounts, policies, the deed, the car title, online logins and where the originals are kept.
If the family will be together over the holidays, it's a good week to talk it through; see the Thanksgiving paperwork talk.
General information checked November 10, 2026. A checklist, not legal, insurance or benefits advice. We are notaries, not lawyers: we can witness signatures and notarize, but we can't tell you which document to sign or prepare one for you.