This pilot study explored a technology-based intervention aimed at increasing student and family engagement in school, using a quasi-experimental pretest-posttest design. All fourth- and fifth-grade students participated in a classroom-based one-to-one program; some students also received take-home tablets and broadband access. Student surveys assessed behavioral, cognitive, and affective engagement and academic motivation. Parent surveys assessed perceptions of school support, empowerment in schools, and overall experiences in schools. Teachers participated in a focus group to share their impressions of the program. Results showed that affective engagement and academic motivation decreased for all students, with no differences between the intervention and comparison groups. Parents in the intervention group reported greater perceptions of school support but no significant differences or changes in empowerment or overall school experiences. Students, parents, and teachers all reported positive experiences with the program. Findings point to the ways varying contexts may influence engagement in school.