Individuals may be able to deduct their Health Insurance premiums under certain circumstances. The deductibility of Health Insurance premiums depends on various factors such as the individual's tax filing status, the type of Health Insurance plan, and whether the individual is self-employed. Generally, Health Insurance premiums can be deducted if they are not paid for with pre-tax dollars and if they meet the criteria for being an eligible medical expense. It's important to consult a tax professional or refer to the latest IRS guidelines for specific details regarding the deductibility of Health Insurance premiums.