We present new parsec-scale resolution data from a multi-phase study of the ISM in the walls of Galactic supershells. Hi synthesis images and CO survey data reveal a wealth of substructure, including dense-tipped fingers and extended molecular clouds embedded in shell walls. We briefly consider formation scenarios for these features, and suggest that both the interaction of an expanding shell with pre-existing dense clouds, as well as in-situ formation of CNM and molecular gas, are likely to be relevant. Future work will also examine the role of instabilities in structure formation and breakup, and will investigate the presence of high-altitude gas associated with supershells and chimneys.