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How do I keep health insurance between jobs?

Updated Sep 3, 20261 min readAnswer
On this pageShort answer What to do Common questions Related questions Sources
Short answer

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.

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What to do

1Price a Marketplace plan first:subsidies favor the between-jobs window.
2Hold COBRA in reserve:60 days to elect, retroactive to day one.
3Spouse's plan? Ask within 30 days:that window is shorter.
4Income dropped hard? Apply for Medicaid:it enrolls year-round.

Common questions

How do I keep health insurance between jobs?

Losing job-based coverage is itself a key that opens several doors - you will not be uninsured unless you choose it. Door one: COBRA, which keeps your exact plan running for up to 18 months, but you pay the full premium (your old share plus your employer's) plus 2 percent - continuity at a sticker-shock price; you have 60 days to elect it, and it can be retroactive to the day coverage ended. Door two: the Marketplace, where losing job-based coverage triggers a Special Enrollment Period - pick a plan within 60 days, and income-based subsidies often make this dramatically cheaper than COBRA. Door three: a spouse or partner's employer plan - losing your coverage is a qualifying event there too, usually with a 30-day ask, so move fast. Door four: Medicaid, which accepts applications year-round and responds quickly when income drops. The strategic order for most people: price the Marketplace plan first (subsidy math favors the gap between jobs), keep COBRA as the fallback you can elect retroactively if a big medical need appears inside the 60 days, and never leave a known procedure or pregnancy floating across a coverage gap. Pymander is a free AI doctor, 24/7 by text, that can help you think through the choice.

About this page. Written and maintained by the Pymander Health team. Last updated September 3, 2026.

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