text: taxability of benefits paid with pre tax dollars? if i pay my insurance with pre tax dollars can i be taxed on a benefit i recieve? depends on the insurance.  health insurance = no.   disability insurance = yes  life insurance = no  supplimental (aflac) = yes  -- any tax advice included in this written communication was not intended or written to be used, and it cannot be used by the taxpayer, for the purpose of avoiding any penalties that may be imposed by any governmental taxing authority or agency.