Why would you have two health policies? Is one a supplemental to your base policy? Generally a major medical policy will coordinate benefits if there is more than one policy in force on the same individual. I would consult your tax adviser as far as the ability to deduct both premiums but quite honestly you are spending a lot more than you need too if both are Major Medical. If you have a Major medical and a policy to supplement the major medical policy, designed to help pay your deductibles then my reaction would be yes you can. Verify this with your tax adviser however.