If it's not pre-tax you can include it in your medical expenses for a possible itemized deduction. But most employer health insurance premiums are deducted pre-tax. Check with your employer.
You cannot claim itemized deductions with TurboTax Free Edition. If your itemized deductions are more than your standard deduction you will have to upgrade to Deluxe or use the CD/Download TurboTax software in order to claim the itemized deductions. Keep in mind that medical expenses are reduced by 10% of your AGI (7.5% if you are 65 or older). Only what remains is deductible.
