Research has demonstrated the importance of family, peer, and community relationships as they relate to adolescents’ development (Crockett et al., 2012; Mann, Kristjansson, Sigfusdottir, & Smith, 2015; Pinquart, 2017: Piquero & Brame, 2008; Wallace et al., 2008). This study investigated adolescents’ perception of support and if their level of support influenced their behavior at school. In particular, this study investigated if adolescents’ perceived maternal figure support predicted their levels of discipline infractions at school. Additionally, variables such as hope, neighborhood connectedness, and gender was investigated to determine if such variables could influence the potential relationship between adolescents’ perception of maternal figure support and their level of discipline infractions at school. The sample size for this study consisted of 800 8th graders who participated in the Mobile Youth Survey from 2006-2009. Two sources of data were used in the present study: Mobile Youth Survey (MYS) was used to identify adolescents’ support systems and the MYS discipline data from the Mobile County Public School System (MCPSS) school records was used to determine adolescents’ level of discipline infractions at school. Results from the study showed that there was no significant relationship between maternal figure support and adolescents’ levels of discipline at school. However, results indicate that maternal figure support was a significant predictor of hope and hope significantly predict adolescents’ level of discipline infractions at school. Furthermore, findings also reveal that maternal figure support significantly predict neighborhood connectedness. Conversely, neighborhood connectedness did not significantly predict adolescents’ level of discipline infractions at school. When addressing potential gender differences within the mediating effects of hope, neighborhood connectedness, and the relationship between maternal figure support and adolescents’ levels of discipline infractions, results conclude that gender did not significantly influence the moderated interaction models for hope and neighborhood connectedness.