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I am considering leaving my current employer. Hypothetically, assume my new employer has a different health insurance provider (although, it probably doesn't matter, since it would be a different group policy).

My current plan is a high-deductible plan with an HSA that my current employer funds with half of the year's deductible. My plan also has an annual out-of-pocket max per person in my family and for the whole plan. We have already had a few appointments that have ticked away at that annual max, but I fully expect to blow past it (on my wife's oop max, at least) when my wife gives birth to our second daughter in June. Thus, a large portion of the hospital stay for my wife and subsequent trips to the hospital will effectively be free for her after she goes into labor, due to hitting her annual limit. She had a major issue post-delivery with our first related to her spinal, so, while not expecting a repeat, there is precedent for follow-up hospitalization.

So, my concern is this:
If I change providers, my understanding is that limit would reset at the new insurance provider. Do I have any options to mitigate this?

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The HSA will continue, and you can use it with the new company even if they don't have a HSA or high deductible plan. If they gave you money lump sum to cover the deductible then that should remain in your account. If they are giving you money every paycheck, then it will stop when the paychecks stop. Check the plans paperwork to make sure.

You will have to look carefully at the options with the new company to decide which plan for the rest of the plan year makes the most sense. You will have to run the numbers to decide if a high deductible, or a co-pay based plan make the most sense. Look at the premiums, co-pays, deductibles, and out of pocket maximums.

Changing insurance might also mean changing your doctors, or even the hospital where the baby will be born.

Note that with the birth of a child you would be able to make changes to your insurance, because that is considered a life event. If this was your first child you would have to change to a family plan.

If you have a choice of when you switch companies it might be better to wait after the child is born for logistical reasons, even if it doesn't make sense for financial reasons. You don't want to walk into the delivery room with coverage but without having an insurance card. It could take months before everything gets reimbursed. If you don't have choice you want to understand how COBRA coverage works.

If you know that the new company will not have an HSA, and you will be getting a check for unused vacation, or severance, then you might want to maximize the money you put into the HSA now to maximize the benefit.

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