Iodine-containing volatiles are major degradation products of halide perovskite materials under irradiation, yet iodine diffusion kinetics into and throughout organic hole transport materials (HTMs) and consequent reactions are largely unexplored. Here, we modify the Ca:O2 corrosion test to Ag:I2 to quantify I2 transmission rates through common organic HTMs. We observe I2 permeability to inversely correlate with HTM ionization energy, or the highest occupied molecular orbital (HOMO) energy. Tracking electronic conductance during exposure to I2 confirms shallow HOMO HTMs are strongly oxidized (i.e., doped), leading to substantial I2 uptake and increased transmission rates. Finally, relationships between HOMO level, doping, and transmission rate are maintained when methylammonium lead triiodide (MAPbI3) photolysis products are the only source of iodine. While HTM energetics influence the initial performance of halide perovskite devices by selective charge extraction, our results further suggest they will affect device stability; deeper HOMO energy HTMs will suppress iodine migration and associated degradation mechanisms.