Through combining the methodology of portraiture with the epistemological stance of youth participatory action research, this article positions Latino/a youth as experts with their encounters with the school-to-prison pipeline. This article examines what it's like to live within the tight and probational spaces of criminal justice-based school discipline practices. Following the journey of a Black Dominican female high school student, the data from this New York City-based youth participatory action research project find three specific processes of dispossession through which Latina/o youth are profoundly affected by the school-to-prison pipeline: institutional abandonment as disinvestment in young people's personhood, social isolation, and deprivation of agency and self-control.