The transition to middle school when children are 10 or 11 can be difficult for employed-parent families; often they must fashion new after-school arrangements in a context of limited options and conflicting views about appropriate care. Based on interviews in a California city with 22 preteens and 26 of their working-class through upper-middle-class parents, this article examines how families negotiated those arrangements. The transition to middle school entailed an abrupt drop-off in school-based care resources and school-to-parent communication and emboldened most of the preteens to press for more autonomy. Some families slipped into self-care arrangements, usually despite parents' misgivings; others pieced together complicated plans for after-school coverage. The author analyzes structural and cultural factors that influenced family negotiations and discusses how middle schools and their communities can be more responsive to the needs of employed-parent families.