This article is about the use of trained Asian elephants (Elephas maximus) for transportation, in particular across muddy or flooded terrain, clandestine off-road transportation, and during guerrilla operations or political revolts. In a sense, these are all in fact the same transport task: the terrestrial conveyance of people and supplies when, due to weather or politics or both, roads cannot be used. While much recent work from fields such as anthropology, geography, history, and conservation biology discusses the unique relationship between humans and trained elephants, the unique human mobilities opened up by elephant-based transportation has been for the most part overlooked as a research topic. Looking at both historical and recent (post–World War II) examples of elephant-based transportation throughout South and Southeast Asia, I suggest here that this mode of transportation has been especially associated with epistemologically less visible processes occurring outside of state-recognized, formal institutions.