The first systematic attempts to straighten the River Inn in Tyrol for shipping and land reclamation date back to the middle of the 18th century. A dedicated hydraulic engineering authority—the so-called Main Ark Inspection—was established to realize this challenging task. The one-man authority was unable to straighten the Alpine river through the period of its existence up to 1792. The reasons for this were by no means related to a lack of technical resources and knowledge. On the contrary, a micro- and environmental-historical analysis of the attempts to straighten the River Inn highlights the complexity of the causes, which were mutually reinforcing and multifactorial. In this paper, four key causes are examined in more detail: (1) the social organization of water engineering, (2) social conflicts between riparian communities among themselves and with the hydraulic engineering authority, (3) conflicts between Tyrol and Bavaria at the wet border downstream of Kufstein, and (4) increased bedload discharge into the main river by tributaries. To illustrate the causes mentioned above, historical river maps are analyzed in great detail, drawing on contemporaneous written sources. The approach thereby highlights the overall complexity of pre-modern hydraulic engineering in all its facets, be they social, technical, natural, administrative, or organizational. To conclude, the results of this environmental history research are embedded and discussed in the context of integrated river management in the Anthropocene.