tax break for health insurance?

Question

I am paying for my health insurance myself not my employer. Means I am paying from my post tax income.

Is it possible to apply this amount as itemised deductible?

Also is there any option to pay this amount from my pre tax income?

Answer 1

Yes you may itemize it on Schedule A. If your company offers a Health Savings Acount then you may pay that amount from your pre tax income

Answer 2

Yes it's an eligible itemized deduction as medical expense. But remember that only the amount of eligible medical and dental expenses that's over 7.5% of your adjusted gross income can be deducted. And no, you can't pay it yourself from pre-tax income.