As the needs of society changed, states faced increasing pressure from the federal government to raise educational standards. States adopted rigorous standards, however many students failed to meet defined proficiency levels, necessitating summer school attendance or grade retention. Factors associated with academic failure have been extensively documented in the academic literature. The factors identified in the research can be organized into six categories, including motivation, age and ability, withdrawal from school, parents and guardians, school practices, and teacher practices. The purpose of the current study was to explore middle school students’ perceptions of factors which contributed to the academic outcomes necessitating enrollment in academic courses in summer school, and what factors they believe could have made a positive impact. This study focused on the following research questions: How did middle school students, enrolled in one or more academic courses in summer school, perceive (1) academic outcomes and to what these were attributed, (2) the relationship among ability, effort, and outcome, (3) sources and levels of motivation, (4) sources and levels of school bonds, (5) interactions and relationships with school personnel, and (6) the role and level of involvement of adults in their academic lives? A qualitative, ethnographic design, with detailed descriptions of the methodological considerations and rich, thick narrative, was used to explore the research questions. Seventeen middle school students, repeating academic courses in summer school, were interviewed. Emergent themes were identified from inductively coded interviews. The analysis revealed that participants primarily accepted responsibility for academic outcomes but also identified distractions as a contributing factor. Teachers were seen as playing a role in both creating and removing distractions. Participants perceived work ethic as positively correlated with intelligence, and perceptions of ability tended to be related to duration of exerted effort. Negative social bonds were perceived as adversely affecting participants’ academic performance, and participants reported few positive interactions or relationships with school personnel. Negative consequences were the primary means used by adults to motivate participants, and too little, too late characterized active adults engagement in participants’ academics. Perceived levels of effort exerted and concern exhibited by an adult paralleled academic outcomes.