Children with disabilities are more likely to engage in some form of challenging behavior. The present study sought to investigate the prevalence of challenging behaviors, such as aggressive/destructive or stereotypic behavior, and identify those personal and contextual risk markers associated with the occurrence of challenging behaviors. A total of 205 children with intellectual disability enrolled in a special education school participated in this study. Fifteen professionals participated in this study and responded to two questionnaires via an interview format. Of the sample, 60% were identified as displaying some form of challenging behavior. Both personal and environmental factors within this school were identified as significant predictors of at least one form of behavior. Findings highlight the need to invest in further research to identify personal and environmental variables that may act as risk markers for challenging behaviors in a specific educational setting to customize the services and supports provided.