The transformation of US punishment in the late 20th century was defined not just by mass imprisonment, but the growth of a shadow carceral state of administrative and civil sanctions, including technical violations of probation and parole that smooth the pathway to prison. We consider the role of technical violations in the shadow carceral state through the lens of lived experience, analyzing interviews with adults on probation in Hennepin County, Minnesota, conducted in 2019. Building on the concept of legal envisioning, we ask how people subject to probation experience the threat of violations and what they imagine would be helpful to avoid them. Ultimately, these perspectives illuminate the need for transformative changes to dismantle the shadow carceral state and raise challenging questions about the role of care in punishment.