Regional identity does not always neatly correspond to geography. In the cognitive conception of many people, Appalachia is located firmly in the American South although the official boundaries range from Alabama to New York. There are undoubtedly differing levels of regional affiliation even by people who orient toward the region. The core area of Appalachian identity, with the strongest regional affiliation, is located in the Southern Appalachian subregion and includes eastern Tennessee, western North Carolina, southwestern Virginia, eastern Kentucky, and southern West Virginia. The present case study investigates the idea of rootedness, or connection to the conceptual Appalachia, taking/AI/monophthongization, a classic Southern feature, as a marker of rootedness. Tokens from a single speaker born and raised in East Tennessee, are examined at two different times. As a high school student, the speaker produces almost categorical monophthongal/AI/; however, as a professional in her mid-30s, the speaker is almost categorically diphthongal. This stark change in linguistic behavior undoubtedly has many sources, yet the speaker discusses how her orientation to the region changed dramatically. The current study furthers our understanding of how speakers negotiate a nuanced Southern and Southern Appalachian regional identity identity and employ linguistic resources to reflect shifting orientations.