Gamma-ray experiments seeking to detect evidence of dark matter annihilation in dwarf spheroidal galaxies require knowledge of the distribution of dark matter within these systems. We analyze the effects of flattening on the annihilation (J) and decay (D) factors of dwarf spheroidal galaxies with both analytic and numerical methods. Flattening has two consequences: first, there is a geometric effect as the squeezing (or stretching) of the dark matter distribution enhances (or diminishes) the J-factor; second, the line of sight velocity dispersion of stars must hold up the flattened baryonic component in the flattened dark matter halo. We provide analytic formulas and a simple numerical approach to estimate the correction to the J- and D-factors required over simple spherical modeling. The formulas are validated with a series of equilibrium models of flattened stellar distributions embedded in flattened dark-matter distributions. We compute corrections to the J- and D-factors for the Milky Way dwarf spheroidal galaxies under the assumption that they are all prolate or all oblate and find that the hierarchy of J-factors for the dwarf spheroidals is slightly altered (typical correction factors for an ellipticity of 0.4 are 0.75 for the oblate case and 1.6 for the prolate case). We demonstrate that spherical estimates of the D-factors are very insensitive to the flattening and introduce uncertainties significantly less than the uncertainties in the D-factors from the other observables for all the dwarf spheroidals (for example, for a typical ellipticity of 0.4). We conclude by investigating the spread in correction factors produced by triaxial figures and provide uncertainties in the J-factors for the dwarf spheroidals using different physically motivated assumptions for their intrinsic shape and axis alignments. We find that the uncertainty in the J-factors due to triaxiality increases with the observed ellipticity and, in general, introduces uncertainties of a factor of 2 in the J-factors. We discuss our results in light of the reported gamma-ray signal from the highly flattened ultrafaint Reticulum II. Tables of the J- and D-factors for the Milky Way dwarf spheroidal galaxies are provided (assuming an oblate or prolate structure) along with a table of the uncertainty on these factors arising from the unknown triaxiality.