Health Insurance Between Jobs
Leaving a job is one of the few moments when you can change health insurance outside of open enrollment. You usually have three paths, and the right one depends on how long the gap will last and how healthy you are.
When your employer coverage actually ends
Most employer plans end on the last day of the month you leave, not your last day of work. Some end the same day. Ask HR for the exact date in writing, because every option below is measured from that date.
Option 1: COBRA
COBRA lets you keep the exact plan you had, usually for up to 18 months. The catch is cost. Your employer was likely paying most of the premium, and under COBRA you pay all of it plus a small administrative fee.
- You have 60 days from the notice to elect it, and it is retroactive to the day coverage ended.
- Good fit if you are mid-treatment, have met a big deductible this year, or need a specific doctor.
- Poor fit if you are healthy and the gap could last more than a month or two.
Option 2: Marketplace special enrollment
Losing employer coverage opens a 60-day special enrollment period on the ACA marketplace. These plans accept everyone regardless of health, and your premium depends on your household income for the year.
- If your income is dropping, you may qualify for a subsidy that makes a marketplace plan the cheapest option.
- If your income is staying high, or you earn too much for a subsidy, marketplace premiums without help can be the most expensive option on this page.
Option 3: A private plan you can start any month
Private, medically underwritten plans do not use enrollment windows. You apply, answer health questions, and if approved you pick a start date. For people in good health these plans often come with lower monthly cost and a broader PPO network than an unsubsidized marketplace plan.
- Approval is based on your health history, so they are not the answer for everyone.
- Many clients use one as a bridge until a new employer plan starts, then keep it anyway because the numbers work.
How to decide in five minutes
- Write down the date coverage ends and when a new employer plan could start.
- Estimate your household income for this calendar year, not last year.
- List any ongoing treatment or prescriptions.
- Send me those three things. I will show you COBRA, marketplace and private side by side, and tell you which one I would pick in your spot.
I do not charge a fee. The carrier pays me, and I show you the options I do not sell when they fit better.
Frequently asked questions
How long can I go without health insurance between jobs?
There is no federal penalty for a gap anymore, but a gap of even a few weeks is a financial risk and some private plans ask about recent coverage. If your gap is under a month, COBRA's retroactive election can cover you after the fact. For anything longer, enroll before the old plan ends.
Is COBRA always the most expensive option?
Usually, but not always. If you have already met a large deductible this year, keeping the same plan through COBRA can cost less overall than starting over on a new deductible.
Can I get a private plan if I have a pre-existing condition?
It depends on the condition. Private plans are medically underwritten, so some conditions are declined or excluded. In that case the marketplace special enrollment is the guaranteed path and I will help you with it.
What if my new job's coverage has a 90-day waiting period?
That is a common reason people use a private plan or short-term bridge. You pick a start date, keep it for the waiting period, and cancel when the employer plan starts.
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Written by Frank Caballero, licensed insurance producer, NPN 21032307. Last updated 2026-10-16. General information, not tax or legal advice.