Gravitational microlensing is one of the most sensitive methods we have to search for macroscopic dark matter. NASA’s upcoming Roman Space Telescope will dramatically advance this search by performing a comprehensive microlensing survey of the Galactic Bulge at sensitivities orders of magnitude stronger than existing telescopes. Its unprecedented sensitivity will provide the opportunity to search for dark matter across a wide range of unexplored parameter space; however, it will also pose new challenges, including an irreducible astrophysical background in the form of free-floating planets. In this talk, I will discuss how population-level modeling can help mitigate this background and open the potential for Roman to make a first discovery of macroscopic dark matter in our galaxy.