Understanding the challenges that students with literacy learning difficulties (LLD) face in their psychosocial development should be a fundamental focus for teaching practitioners and researchers. While success in literacy development is acknowledged to be integral, not only to success within the educational context but also to how individuals navigate through local and global society, less attention has been paid to the difficulties in psychosocial development that often accompany difficulties in literacy development. The pervasive nature of LLD can influence students’ ability to positively adapt to stressors within their lives. While research has typically focused on the remediation of psychosocial development and literacy development as separate entities, other research has targeted psychosocial development via the remediation of literacy difficulties. The current research adds to existing literature by examining the association between psychosocial and literacy development via an academic intervention in students with LLD. The primary focus of the current research was whether the psychosocial development of students with LLD in Year 4 to Year 6 (U. S. Grades 3 to 5) could be affected via a targeted literacy intervention. Study 1 included instruction in general literacy skills, focusing primarily on decoding and fluency in reading text at or above the reading level of the student. Study 2 and Study 3 further included specific instruction in morphological and orthographic awareness. The effectiveness of the targeted intervention at improving students’ literacy development was assessed, along with changes in measures of self-esteem, self-efficacy, and resilience. Findings supported the notion that psychosocial and literacy development of students with LLD could be positively influenced via such targeted interventions. However, gains in self-efficacy and resilience seem to be dependent on the levels of resilience at preintervention. Interventions that aim to positively impact on psychosocial, as well as, literacy levels in children with poor literacy acquisition; therefore, may need to be considered against the child’s existing psychosocial development.