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What if someone gets killed because of some clear bug/error and the jury decides to award 100s of millions just for that single ? I’m not sure it’s trivial to insurance companies to account for that sort of risk

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It is trivial and they've done it for ages. It's called reinsurance.

Basically (_very_ basically, there's more to it) the insurance company insures itself against large claims.

I’m not sure Boeing etc. could have insured any liability risk resulting from engineering/design flaws in their vehicles?

Not trivial, but that is exactly the kind of thing that successful insurance companies factor into their premiums, or specifically exclude those scenarios (e.g. not covering war zones for house insurance).

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