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Why is company provided health insurance tax free, but individual health insurance is not?
The idea is that the premiums (or costs) associated with the plan are a business expense, you know that already.  The distinction here is that employees don't pay premiums, they elect to contribute. The company sponsors a plan, the employees then choose to accept less salary in order to participate in the employer's plan.  The idea is that you're foregoing income. Why is the employee not taxed on this cost?  One major reason is that the employee has no say in, and often no idea, what the gross costs are (some find out if they ever receive COBRA election paperwork). There are more benefits than strict healthcare that are Section 125 eligible.  The government has a vested interest in keeping the population healthy, and when the ERISA laws and Section 125 were written it was (and still is) a pretty low friction way to get health insurance out to more people.  At this point, taking away the tax break from the employees would be a huge government take away from most of the population.  Try to get a politician to take something away from taxpayers. Why doesn't the deduction exist in kind to people buying individual coverage?  Ask your legislators.  There are thousands of preferential tax treatment oddities, where some industry will get some sort of benefit or break.  I'm not sure what leads you to think there needs to be some supremely logical reason for this oddity to exit.