This study aims to understand Chilean parents’ and adolescents’ conceptions of autonomy and whether they hold different expectations for autonomous behaviors by generation and socioeconomic level. A qualitative approach to data collection was used through separate focus groups of parents and adolescents from different socioeconomic condition. Substantial similarities in parents’ and adolescents’ conceptions of autonomy were found. Both generations conceive autonomy as multidimensional (i.e., self-sufficiency, decision making, and acting responsibly) and as an age-graded process that is achieved in interaction with parents. Participants emphasize the affective quality of the parent–adolescent relationship, particularly trust, for healthy autonomy achievement. Differences by socioeconomic status (SES) were also apparent in that low-middle-SES parents emphasize the self-sufficiency and responsibility component of autonomy, and adolescents grant more authority to parents in regulating adolescents’ behavior compared with their high-middle-SES counterparts