This exploratory study examines how frontline managers in a natural resource extraction context make sense of natural systems. The goal is to extend ecological sensemaking theory while also expanding organizational theory further into the frontlines of natural resource extraction industries. To do so I examine how particular characteristics of interacting with natural systems influence how frontline managers in commercial trawl fishing in Alaska make sense of those systems. These characteristics are ‘irreversibility’ and ‘indeterminacy.’ ‘Irreversibility’ is the unyielding march of time inherent to organizing processes and ‘indeterminacy’ is an inability to know for certain how organizing processes will play out over time. Ecological sensemaking functions as a conjectural process at the frontline of the Alaskan commercial fishing context. After elaborating these novel characteristics of ecological sensemaking theory, the chapter offers suggestions for next steps in practice and research.