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Denied But Heard

Denied But Heard Signing up for Medicare or Medicaid, explained

Signing up for Medicare or Medicaid.

Sign up for Medicare Part A and Part B through Social Security, not Medicare. Turning 65, your window is 7 months long; retiring later with job-based coverage, you have 8 months after that coverage or job ends, and COBRA doesn’t count. You can apply for Medicaid any time of year.

Updated October 23, 2026. General information, not legal advice. Your policy, plan documents and state rules control.

Signing up for Medicare or Medicaid.

You just retired, or you’re turning 65, or you’re helping a parent, and the sign-up makes no sense. It isn’t you. The rules are confusing, and a missed deadline can cost you every month for as long as you have the coverage. Here’s the short version, and who to call.

  1. Sign up through Social Security, not Medicare

    Apply for Medicare Part A and Part B online at ssa.gov/medicare/sign-up. To do it by phone, call Social Security at 1-800-772-1213 (TTY 1-800-325-0778), Monday to Friday, 8 a.m. to 7 p.m., and make an appointment. If you already get Social Security benefits before you turn 65, you’re signed up for Part A and Part B automatically, and your card comes in the mail about 3 months before your coverage starts.

  2. Know your sign-up window

    Turning 65: your window is 7 months long. It starts 3 months before the month you turn 65 and ends 3 months after it. Retiring after 65 with job-based coverage: you have until 8 months after the job or that coverage ends, whichever comes first. COBRA and retiree coverage don’t count as job-based coverage, and they don’t stretch that window. Missed both? The general sign-up period is January 1 to March 31 each year.

  3. Had insurance through a job? Prove it.

    Apply for Part B online, then ask your old employer to fill out Section B of form CMS-L564, which shows you had job-based coverage. Mail or fax it to your local Social Security office. If the employer can’t fill it out, complete Section B as well as you can, don’t sign it, and send proof of your job-based insurance with it.

  4. Don’t skip drug coverage

    If you go 63 days or more without Part D or other drug coverage that’s as good, a penalty is added to your premium for as long as you have Medicare drug coverage, even if you switch plans. Signing up late for Part B adds 10% for each year you could have had it, usually for as long as you have Part B.

Medicaid, and help paying for Medicare

  • Medicaid: you can apply any time of year, through your state Medicaid agency or through HealthCare.gov. Medicaid.gov lists each state’s agency and phone number.
  • Can’t afford the premiums? A Medicare Savings Program can have your state pay your Part B premium. Some also pay Part A and Part B deductibles, coinsurance and copayments. Apply through your state Medicaid office.
  • Extra Help lowers drug plan costs. You get it automatically if you have full Medicaid, a Medicare Savings Program or SSI. Otherwise, apply through Social Security.
  • Nursing home or long-term care through Medicaid? Asset limits vary by state, and Medicaid looks back 60 months at money or property given away. Talk to your state Medicaid agency before moving assets.

“Open enrollment” isn’t your sign-up. The October 15 to December 7 period you hear about is for people who already have Medicare and want to change plans.

Free one-on-one help: your state’s SHIP (State Health Insurance Assistance Program) counselors help with sign-up, Medicare Savings Programs and Extra Help, at no cost.

Sign up for Medicare (Social Security) (opens in a new tab) When you can sign up (Medicare.gov) (opens in a new tab) Signing up after job coverage, form CMS-L564 (Medicare.gov) (opens in a new tab) Avoid late penalties (Medicare.gov) (opens in a new tab) Extra Help with drug costs (Medicare.gov) (opens in a new tab) Find your state Medicaid agency (Medicaid.gov) (opens in a new tab) Apply for Medicaid (HealthCare.gov) (opens in a new tab)

General resources, checked October 16, 2026, from Social Security, Medicare.gov, Medicaid.gov and HealthCare.gov. Not legal or financial advice. Medicaid rules and limits vary by state; your state Medicaid agency has the final word.

Quick answers

Does COBRA count as job-based coverage for Medicare?

No. COBRA and retiree coverage don’t count as job-based coverage, and they don’t extend your Medicare sign-up window.

How do I avoid the Part D late penalty?

Don’t go 63 days or more without Part D or other drug coverage that’s at least as good. The penalty is added to your premium for as long as you have Medicare drug coverage.

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