Star-forming galaxies are known to host multiphase outflows, many of which span many orders of magnitude in density and temperature and extend many kiloparsecs out into the circumgalactic medium (CGM). Along with this large range in phases comes a large range in physical scale — the largest structures may span kiloparsecs, while the smallest structures may be sub-parsec in size or less. Understanding the full range of cloud scales is essential in order to make accurate comparisons between simulations and observational data. To that end, in this talk I will discuss cloud-scale structure in outflows and the CGM in two contexts. First, I will present cloud structure in CGOLS, the best resolved simulations of starburst outflows to date. Second, I will discuss CloudFlex, a promising new parametric model that can step in where the resolution of hydrodynamic simulations falls short.