Andrew Monroe [pseud.] (b. 1894) was a Colorado street kid whose acts of truancy and theft landed him before the state's early juvenile courts, and his youth was marked by attempts at escape from reform school. His childhood and youth provide insights into the mechanics of how systems of juvenile corrections operated in the early twentieth century. To enforce new truancy laws, Progressive Era child-savers relied on report cards for the surveillance of probationers, categorizing children like Andrew as "stubborn," "unyielding," and "disobedient." Ultimately, Andrew's refusal to comply with these new forms of institutional control serves as a case study for the challenges that children faced in escaping an apparatus that reduced them to the label of "delinquent."