Vocations · Professional Development

Turning 65,
on the right dates.

Medicare has a seven-month window around a 65th birthday, a separate eight-month window after a job ends and late penalties that last for life. Enter a birth date and current coverage and the dates and the decisions that apply come out in plain words.

Add a personWhat you get

Your timelines

The worked example is made up: a worker on a large employer’s plan with an HSA, a retiree on COBRA whose birthday is on the first, and someone who let the window pass. Saved on this device only.

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What you get

Vocations · Professional DevelopmentFree

What you finish with
A record per person: birth date, Social Security benefits, current coverage, employer size, the date the job or coverage ends and HSA contributions; six planning steps. Works out the Initial Enrollment Period (moving a month earlier for a birthday on the 1st), the sign-up date for Part B to start on time and the 8-month Special Enrollment Period after large-employer coverage; flags the window, the General Enrollment Period and penalties, COBRA, small employers, the Marketplace, HSAs and automatic enrollment.
Who it is for
Adults approaching 65, people working past 65, and adult children helping a parent plan.
Format
Browser guide with a saved record per person. Prints one person’s dates and decisions, every person in a table or a blank form; downloads a spreadsheet (.csv); exports and imports a file.
Access
Free. No account, no sign-in and nothing to install. Everything you type stays in this browser; nothing is sent to Caveat.
Where it lives
The Professional Development space in Caveat Vocations.
Support
Questions about access, an order or a correction: team@caveatacademic.com.

How to use it

  1. Enter the birth date exactly; the 1st of the month changes the window.
  2. Choose the coverage you have now and the employer size.
  3. Read the dates and decisions the page gives.
  4. Sign up at ssa.gov in the window, or keep proof of job-based coverage.
  5. Compare plans before the Medigap window opens.

Add a person

The window around 65

The 7-month window around a 65th birthday3 monthsbefore2 monthsbefore1 monthbeforeBirthdaymonth1 monthafter2 monthsafter3 monthsafterSign up in the blue months: Part B starts the first day of the birthday month.Sign up in the birthday month or later: it starts the month after you sign up.Born on the 1st? Everything moves one month earlier.The 7-month window−3−2−1B+1+2+3Blue months: Part B starts the firstof the birthday month. B = birthdaymonth. Later: the month after yousign up. Born on the 1st? One monthearlier.
Part B start dates follow the rules in effect since January 2023.

Penalties

Signing up for Part B late without job-based coverage adds 10% to the premium for each full 12 months you could have had it, for as long as you have Part B. The Part D penalty is 1% of a base premium for each month without creditable drug coverage.

Medigap

Your Medigap open enrollment period lasts six months from the first month you have Part B and are 65 or older. During it, insurers cannot refuse you or charge more for health conditions; after it, in most states they can.

Sources

  1. Medicare.gov. When does Medicare coverage start?, Avoid late enrollment penalties and Working past 65 (medicare.gov).
  2. Social Security Administration. Medicare (Publication 05-10043) and Applying for Medicare only (ssa.gov).
  3. Internal Revenue Service. Publication 969, Health Savings Accounts: eligibility ends with Medicare enrollment (irs.gov).
  4. Centers for Medicare & Medicaid Services. Choosing a Medigap Policy (medicare.gov).

The worked example is made up. This page explains the federal rules in general terms; it is not financial or legal advice, and Social Security and Medicare decide eligibility. Nothing you type is sent to Caveat. Support: team@caveatacademic.com.