What's inside
A timeline checklist and three worksheets.
- 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.
- 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.
- Worksheet 1, the coverage-bridge comparison: COBRA, Marketplace, spouse's plan and retiree coverage, compared on 12 questions.
- Worksheet 2, annual cost: expected cost versus worst-case cost for each option.
- Worksheet 3, the Marketplace income (MAGI) planner: which retirement cash sources generally count, and which generally do not.
- 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.