Generally, prepaid medical expenses, including dental costs, are not deductible. An old Tax Court case said that advance payment for medical services to be rendered in the following year are not deductible in the year paid. The only exception is for prepaid of lifetime care from a continuing care facility or nursing home.
Payments within one tax year of the entire amount due to a participant in a qualified retirement plan. Qualifying lump sums may be directly rolled over tax free, or, in some cases, are eligible for current tax under a favorable averaging method.