This study examined the key factors influencing the alleviation of academic helplessness among third-year middle school students in Korean society by utilizing data from the 2nd and 3rd waves (2019–2020) of the KCYPS (2018). Structural equation modeling (SEM) was employed to rigorously analyze the structural relationships among these factors. Key research findings are as follows. First, higher parental socioeconomic status (SES) was associated with lower levels of academic helplessness among students, whereas a more controlling parenting style was linked to increased academic helplessness. Furthermore, controlling parenting negatively influenced students' school social capital and grit. Both school social capital and grit functioned as significant protective factors in mitigating academic helplessness. Next, a multi-group analysis was conducted to examine group differences in academic achievement between upper-middle-achieving and lower-achieving student groups. The results revealed that, only within the lower achieving group, lower parental SES was significantly associated with more controlling parenting attitudes. In contrast, in the upper-middle-achieving group, stronger controlling parenting attitudes were found to significantly reduce students' school social capital and increase their academic helplessness. Based on the above findings, the study suggested the necessity of policy interventions to alleviate academic helplessness among middle school students.