In order to use the IRS online tool designed to help you determine if your premiums and other medical expenses are tax deductible, the IRS says that you will the following information: The type and amount of medical expenses you paid. Confirmation that the expenses are for the tax year in question and that they weren’t already reimbursed or paid via a Health Savings Account or an Archer Medical Savings Account. Your tax filing status and adjusted gross income. Because medical expenses likely are just one part of the equation that determines whether you are going to itemize on your tax return, one approach would be to use the tool to determine if a specific medical expense qualifies under IRS rules. Once you know the total amount of medical expenses you can claim, you can use this information alongside other information to determine whether you should itemize. Most financial advisors and tax software will help you determine which medical expenses qualify for deduction and whether you should take advantage.