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The amount with code "DD" in box 12 on the W-2 is the sum of your employer's contributions to your health insurance as well as your contributions to your health insurance as part of a salary reduction program.

By "salary reduction", we mean that you agree to have this amount removed from your Wages as reported on your W-2.

This is why you can't report your "contributions" to health insurance as medical expenses, because they have already been removed from your income. This makes your contributions "pre-tax".

Only if you paid for health insurance premiums with after-tax dollars would you be able to deduct them on Schedule A..