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Currently 90% of pharmaceuticals in the discovery pipeline are hydrophobic, yet such hydrophobic compounds account for only 40% of drugs that are FDA-approved and marketable. Consequently, researchers recognize that there is an urgent need for better delivery mechanisms for hydrophobic drugs to increase efficacy and reduce negative side-effects. Poly(ethylene oxide)-block-polycaprolactone (PEO-b-PCL) is an FDA-approved, biocompatible, amphiphilic block copolymer, making it an intriguing candidate for hydrophobic drug encapsulation and controlled release into the body. In this work, a variety of characterization techniques, including DSC, NMR, and SEM, are employed to investigate the degradation of PEO-b-PCL films within aquatic environments. Previous work shows that the degradation of these films is accelerated in both basic and acidic environments, however there are opportunities to better understand the degradation rate as it relates to the physical structure of the films. This information suggests that pH could be used as an external stimulus to guide the release of hydrophobic compounds encapsulated within the PCL. Through examining the effect of block fraction and crystallinity on the degradation rate and pathway at various pH, the potential of PEO-b-PCL as a delivery agent can be better understood.