While there are clusters of studies on Black feminist methodologies, there is still a need for Black women’s scholarship on transnational field research. Traversing borders provides insight into the racial histories, gender critique, conceptual limits, and imagined possibilities of Blackness under the nation-state. Leveraging the lessons and inquiries from my travel across the United States-Canada border at the Detroit-Windsor tunnel, I model, narrate, and stress the importance of reflection on positionality as an analytical tool. While the reproduction and reinforcement of racial and gender hierarchies rooted in white supremacy are laid bare at the intersection of geographies and identities at the border, this chapter also demonstrates how this grounded, reflective method of analysis works to broaden critiques of imperialism and its connection to gendered anti-Blackness.