For many dark matter models, the annihilation cross section to two-body final states is difficult to probe with current experiments because the dominant annihilation channel is velocity or helicity suppressed. The inclusion of gauge boson radiation for three-body final states can lift the helicity suppression, allowing a velocity-independent cross section to dominate the annihilation process, and providing an avenue to constrain these models. Here we examine experimental constraints on dark matter that annihilates to two leptons plus a bremsstrahlung boson, $\bar{\ell}+\ell+\gamma/W/Z$. We consider experimental constraints on photon final states from Fermi-LAT using both diffuse photon data and data from dwarf spheroidal galaxies, and compare to the implied constraints from 21 cm measurements. Diffuse photon line searches are generally the strongest over the entire mass regime. We in particular highlight the model in which dark matter annihilates to two neutrinos and a photon, and show that these models are more strongly constrained through photon measurements than through existing neutrino bounds.