The US-Mexico border is a contested symbol of coalescing cultures, political tensions, and legal negotiations that frame the relationship between the two countries. In this paper I focus on the implementation of, and challenges to, recent immigration policies in California. Through an analysis of media coverage and Operation Gatekeeper in San Diego County, I illustrate the means by which discussions of safety, legality, and mobility have infused efforts to bound and challenge distinct notions of “US,” “Mexican,” and immigrant identities and spaces. In particular, the increased presence of US Border Patrol agents and the introduction of surveillance technologies has resulted in a border landscape that has been viewed by some groups as providing a safe space for US citizens, while others see these changes to the social and physical landscape as intimidating and discriminatory. In particular, I argue that contradictory uses of surveillance and transportation technology suggest that the border is less a symbol of separation and fixity than an icon of mobility, and as such, points to the significance of the border as a process of journeying across and within cultures.