Contested Southernness deals with the interaction between language, identity, and borders, using Louisville, Kentucky, located at the northern border of the Southern dialect region, as a case in point these interactions that appear to be neither simple nor straightforward. Through an examination of a variety of production and perception data, Louisvillians are shown to vary in their attitudes toward and production and perception of certain linguistic features in a way that indicates that they experience the border as the coming together of at least two distinct regions, one Southern and one non-Southern, seemingly choosing to align or disalign with different ones randomly. Non-Louisvillians, on the other hand, view the urban center as the other in the largely rural state. Using the example of Louisville, identities at the border are shown to be fluid, complex, and dynamic, where speakers constantly negotiate, contest, and shift between identities, in the active and agentive expression of their amplified awareness of belonging brought about by their position on the border.