Recent observations at gamma-ray and radio energies, as well as local observations of charged cosmic-rays, have placed increasingly stringent constraints on the annihilation cross-section of Weakly Interacting Massive Particle (WIMP) dark matter. Excitingly, these studies have begun to rule out the infamous “thermal annihilation cross-section”, where WIMP models are expected to naturally obtain the observed relic abundance. As expected when multiple cutting-edge observations coincide, there is currently tension between different studies. For example, strong limits from gamma-ray searches in dwarf-spheroidal galaxies lie in significant tension with dark matter explanations for the observed “Galactic Center excess” observed near the center of the Milky Way. I will focus on the landscape of current indirect WIMP searches, with a forward-focus on two main issues: (1) Can upcoming multi-wavelength data rectify the tension between current indirect experiments? (2) What future observations will be most effective at observing, or ruling out, the WIMP paradigm?