Watchfulness shapes many Chicanxs’ and other People of Color’s everyday lives in San Diego. Experiencing racist discrimination can lead to becoming vigilant, which frames their subjectivity. Focusing particularly on Chicanxs, we show how they seek to intervene against structural inequalities and threats in their lives, such as by re-claiming space, consciousness raising, participating in protests, and healing practices. We argue that contestations surrounding belonging create particularly watchful selves and that this is a significant aspect of borderland lifeworlds more broadly. The book advances the Anthropology of borders, coloniality, subjectivity, and race, as well as contributing to Chicano and Latino Studies, and Urban Studies. Pushing the boundaries of conventional approaches, this book is methodologically innovative by including team fieldwork, digital ethnography, and illustrative work by a local artist. It fills a gap in Security Studies by examining peer-to-peer vigilance beyond top-down surveillance and bottom-up "sousveillance," and expanding previous understandings of watchfulness as an ambivalent practice that can also express care and contribute to community building, as well as representing a "way of life."