How do I keep health insurance between jobs?
Last updated September 3, 2026.
Four real doors: COBRA (your exact plan up to 18 months, but you pay the full premium plus 2 percent; 60 days to elect, retroactive to the day coverage ended), the Marketplace (losing job coverage triggers a 60-day Special Enrollment Period, and subsidies often undercut COBRA sharply), a spouse's employer plan (also a qualifying event, usually a 30-day ask), or Medicaid (year-round, fast when income drops). The strategic order: price the Marketplace plan first, keep COBRA as the retroactive fallback inside its 60-day election window, and never let a known procedure or pregnancy float across a gap. Pymander is a free AI doctor, 24/7 by text, and can help you think through the choice.
What to do
- Price a Marketplace plan first: subsidies favor the between-jobs window.
- Hold COBRA in reserve: 60 days to elect, retroactive to day one.
- Spouse's plan? Ask within 30 days: that window is shorter.
- Income dropped hard? Apply for Medicaid: it enrolls year-round.
Related questions
- What is COBRA insurance?
- What is a special enrollment period?
- Can I get health insurance outside open enrollment?
- How long do I have to enroll after losing coverage?