Purpose: The purpose of this paper is to use SEM to explore the effects of enabling school structure (ESS) and academic optimism (AO) on school achievement (SA). Design/methodology/approach: A sample of 58 urban schools, including 42 elementary schools and 16 middle schools in a southeastern district in the USA were included in this study. Structural equation modeling was used to test the effects of three exogenous predictor variables (ESS, elementary status, and socio-economic status (SES)) on a latent mediating variable (AO) and a latent dependent variable (academic achievement). Findings: Findings confirm that three factors; collective efficacy, faculty trust in clients, and academic emphasis come together to create the general latent construct referred to as AO by Hoy et al. (2006). Findings also support the importance of ESS in establishing a culture of AO. Together ESS, AO, elementary school level, and SES explained 77 percent of the variance in SA, with AO having the most significant effect above and beyond the effects of SES. Research limitations/implications: This study was based on a sample of schools in the Southern portion of the USA. Findings may not be generalizable to other areas. The lack of availability of individual student achievement data prevented the use of hierarchical linear modeling. Practical implications: Findings from this study point to the importance of administrators establishing flexible rules and regulations and engaging in a leadership style that is collaborative. It appears that ESS not only promotes the establishment of AO but contributes to increased SA and is likely to be critical for upper levels of schooling. Social implications: Reform efforts need to involve parents and community members. AO may provide an appropriate lens to further explore parent and community perceptions of reform efforts and relationships with administrators and teachers. ESS may assist in creating the structures necessary for increased parent and community involvement as well as increased perceptions of AO. Originality/value: This study is one of only three studies known to explore the effects of ESS on AO and is one of the first known studies to explore these effects in a middle school setting.