The Islands of Four Mountains island group of the Aleutian island arc is remote and difficult to access. Consequently, little fieldwork has focused on geomorphic processes and their relationship to island morphology, climatic change, and human settlement. We investigated glacial, fluvial, and slope processes on the morphologically different Carlisle, Cleveland, and Tana volcanoes. The islands were extensively glaciated at the last glacial maximum (LGM), and there is evidence for a Neoglacial advance. On the highly dissected Tana volcano, a large basin is likely the result of a pre-LGM sector collapse and subsequent glacial erosion into weak hydrothermally altered rock. Valley and moraine morphology is also influenced by hydrothermal alteration. On both Tana and Carlisle, there are sediment fans composed dominantly of thick debris flow deposits mantled by ~3 m of layered tephras, fine-grained alluvium, and anthropogenic deposits. Debris flow deposition was favored during the unstable paraglacial landscape of the early Holocene–latest Pleistocene. The earliest direct archaeological evidence for settlement is 3.8 cal ka BP, but soil geochemical evidence suggests that the islands were inhabited by 7.3 cal ka BP. This discrepancy in the archaeological record may be explained by geomorphic processes including coastal erosion and unstable geomorphic surfaces.