Direct observation of the small scale structure of matter in the Universe provides potentially important information about a wealth of physics, from complex galaxy evolution processes to fundamental particle properties of dark matter. Detecting this fine structure in dark matter, though, is notoriously difficult. Dark matter indirect detection--through observation of radiation products of particle annihilation--may be the most direct method for observing small scale structure. However, in an observed signal, the amount of dark matter clustering is degenerate with the annihilation cross section. This talk outlines ways this degeneracy may be broken with indirect detection alone. Scenarios are discussed where either abundant substructure leads to discovery of annihilation radiation (revealing properties of the substructure), or a discovery strongly constrains the presence of significant dark matter halo substructure.