Granted, even on the HSA plan you cannot deduct Critical Illness Insurance or Life Insurance premiums for tax purposes or use your Account to pay for the premiums. More important than tax savings you are protecting your income and your assets. Your income and assets are what supports your family's lifestyle. The remaining premium savings should go towards other long term investments such as Long Term Care, college funding, IRA or other Retirement Portfolio and whatever else you need to help your family to live more comfortable and secure.