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Free healthcare bridge checklist

Retiring Before 65? Build the Healthcare Bridge Before You Give Notice.

Compare coverage options, costs, household income and the handoff to Medicare before your employer coverage ends.

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Retiring Before Medicare Checklist

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Coverage

Compare eligible Marketplace, COBRA, spouse and retiree coverage side by side, including networks and prescriptions.

Income

Understand why expected household MAGI can matter for Marketplace savings, especially with the 2026 rules.

Medicare handoff

Plan age-65 enrollment, HSA timing and a younger spouse's coverage before the bridge ends.

Who it's for

For anyone whose paycheck may end before Medicare begins.

  • You plan to retire, or might be retired early, before 65.
  • Your health coverage comes from your job or your spouse's job today.
  • You expect to live on retirement-account withdrawals, savings or a pension for a few years.
  • You are married and one spouse will reach 65 before the other.
  • You have an HSA and want to understand contribution timing near Medicare.

What's inside

A timeline checklist and three worksheets.

  1. Key dates and deadlines: the coverage end date, the COBRA election window, the 60-day Marketplace Special Enrollment Period, spouse-plan special enrollment, the Medicare Initial Enrollment Period and the HSA cutoff.
  2. Timeline checklist: 6–12 months before leaving work, 60–90 days before, the month coverage ends, each year until 65, and the year before 65.
  3. Worksheet 1, the coverage-bridge comparison: COBRA, Marketplace, spouse's plan and retiree coverage, compared on 12 questions.
  4. Worksheet 2, annual cost: expected cost versus worst-case cost for each option.
  5. Worksheet 3, the Marketplace income (MAGI) planner: which retirement cash sources generally count, and which generally do not.
  6. Questions to ask HR, a Marketplace navigator and your tax professional, plus common mistakes and official help lines.

Sample checklist items

  • Confirm the exact date employer coverage ends for you and any covered family members.
  • Request a COBRA premium estimate for every person who would be covered.
  • Preview Marketplace plans for your ZIP code, including doctors and prescriptions.
  • Estimate household MAGI for each calendar year until 65.
  • Make a separate coverage plan for a younger spouse.
Why 2026 is different: the temporary enhanced Marketplace premium tax credits expired at the end of 2025. For 2026 coverage, households with income above 400% of the federal poverty level ($62,600 for one person or $84,600 for two in the contiguous states) are generally not eligible for a premium tax credit. In addition, excess advance credits must be repaid in full at tax time. The guide includes a labeled hypothetical showing how a small income change near that line can matter. Sources: Congressional Research Service, HealthCare.gov.

Prefer to read first? See healthcare before Medicare and health insurance from 62 to 65.

Education first

Use the checklist to find the questions that need a deeper answer.

The guide does not recommend any insurance plan. Individual recommendations require individual facts and an appropriate advisory process.