Collaborative ventures between families and schools can result in children being successful both academically and in life (Henderson & Berla, 1994; Jackson & Davis, 2000; Mapp, 1997). The most successful predictor of student achievement is an encouraging home environment, high expectations from parents, and parental involvement (Epstein, 2001; Zellmann & Waterman, 1998). Furthermore, Epstein's (2001) Framework for a Comprehensive Program of Partnership lists six types of linkages between school, family, and community that suggest collaboration between school and home is more likely to result in benefit for a child than "separate spheres of influence" (Epstein, 1995, p. 702). What effect might parental/familial involvement have when a student develops a pattern of poor academic achievement? How do schools involve parents when the issue of retention arises? What role do parents play in retention decisions at the middle level? Considerable research has been focused on retention in the early grades and its consequences (Darling-Hammond, 1998; Parker, 2001; Grissom & Shepard, 1989); however, not much has examined retention at the middle level. Extant literature and our earlier, preliminary study on elementary and middle school retention indicate that while retention is largely in disfavor among educators (Alexander, Entwistle, & Dauber, 2003; Jimerson, 2001; Natriello, 1998), it is still pervasive in American schools (Hauser, 2001). However, middle level schools that seek to involve parents, early and often, in conversations about their daughters' and sons' maturity and academic progress increase the likelihood that students will advance successfully from one grade to the next. The lack of literature regarding those relationships has spurred this research. This paper examines the roles and relationships that exist between parents and schools when children are identified as at-risk for grade retention or are retained. Within the paper, three main questions will be discussed: (1) What does retention look like at the middle level? (2) How do schools effectively involve parents in the retention decision making process? And (3) what effect does this have on the decision to retain?