In recent years, school attendance problems have become one of the significant challenges faced by the education sector in our country. To explore the types of outcomes for adolescents with difficulties attending school and their families’ psychological processes, this study employed a case study method. Through public recruitment on various online platforms and communities, we conducted in-depth interviews and follow-up investigations with eight adolescents who voluntarily participated in the research and had experienced school attendance difficulties for more than one semester, along with their parents. The results indicate that the outcomes of adolescents’ school attendance difficulties can be categorized into four types based on their physical and mental states and school attendance status: Stable Reintegration Type, Self-Consistent Stabilization Type, Persistent Stagnation Type, and Turbulent Reintegration Type. These four types may exhibit dynamism and instability. Each type of family experiences different psychological processes: (1) Stable Reintegration Type: Stage One: Parents experience anxiety and conflict, while adolescents feel anxious and seek to avoid school. Stage Two: Parents reflect and take action, leading to a passive relapse in adolescents. Stage Three: Parents provide relief and support, allowing adolescents to rebuild stability. (2) Self-Consistent Stabilization Type: Stage One: Parents feel overwhelmed and helpless, and adolescents experience confusion and distress. Stage Two: Parents persist and seek help, enabling adolescents to process and organize their thoughts. Stage Three: Parents accept and support, leading adolescents to stabilize and achieve self-consistency. (3) Persistent Stagnation Type: Stage One: Parents deny and conflict, and adolescents resist and isolate themselves. Stage Two: Parents experience turmoil and contradictions, causing adolescents to feel chaotic and relapse. Stage Three: Parents feel powerless and stagnate, and adolescents withdraw and become resistant. (4) Turbulent Reintegration Type: Stage One: Parents neglect and avoid, and adolescents struggle with depression. Stage Two: Parents reflect and learn, supporting adolescents in trial-and-error healing. Stage Three: Parents transform and accept, and adolescents persevere amidst turbulence. It is evident that: (1) The recovery process for adolescents with school attendance difficulties is long, winding, and fraught with complexity and uncertainty. (2) The reintegration rate for these adolescents is not ideal. (3) There is an interplay between the psychological processes of adolescents with school attendance difficulties and their parents. Therefore, professionals intervening in school attendance problems must fully recognize the difficulty and complexity of addressing this issue and place great importance on a family systems perspective and working with parents.