My medical insurance contributions are listed on my W-2 Listed in Box 14 Other as "Sec. 125: 5318.46". What does that mean? is it pre-tax or not? Can I claim it?

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Your medical insurance premiums are pre-tax, that is the purpose of the "Sec. 125" plan, you can't claim a deduction on your tax return.

Do you have an Intuit account?