Using data from a longitudinal study, this article traces how in- and out-of-school processes placed youth at the center of a community language tip into English in Piniq, a Yup'ik village in Alaska. During an early phase of language tip, youth underscored bilingual connections to community and place through storytelling with peers. Yet youth were also experiencing linguistic insecurities and losing forms that marked a linguistic orientation to land. Further, adult responses to youth language changes fed vicious cycles of reduced resources for and increasing doubts about bilingualism. Situating and examining young men's seal-hunting stories, the article highlights how youth in the first group to speak mostly English mediated life contingencies, uneven linguistic resources, and apprenticeship experiences as they learned a knowledge system embedded in the life of their community. Implications for educators in rapidly changing linguistic ecologies are discussed. (Contains 2 footnotes.)