Alaskan English (AE), or the regional variety of English used by Native Alaskans, is a unique yet largely underinvestigated phenomenon. Specific conditions in which Alaskan English and its distinct characteristics have emerged remain significantly understudied. The aim of this article is to explore these conditions as well as their long-term effects on the regional native language communities. The present work gives an overview of historical and sociolinguistic factors, the influence of which can be considered crucial as far as the variety and the language situation in Alaska are concerned. The article primarily focuses on the contacts between linguacultural communities during colonization, language policy in various periods of time, the English language acquisition in local educational context as well as language shift. Data from the personal narratives of Upper Kuskokwim Athabaskans is used in the study. Twenty six interviews were recorded during the fieldwork in the Inner Alaskan settlement Nikolai by one of the authors in 2001 and 2019. To describe the consequences of language shift and the process of “shaping” the local variety of English, comparative analysis of the interview transcripts has been employed. This method enabled us to compare and contrast the linguistic realities and the conditions of language acquisition between and within generations. Apart from that, some elements of discourse analysis have been used to reconstruct the sociolinguistic context behind the narrators’ statements. The obtained data sheds light on the sociolinguistic and cultural processes that took part in the region and their influence on the language situation and Alaskan English, and it lays basis for future research into the topic.