This qualitative case study explored administrators' perceptions of family and community engagement activities that enhanced student well-being and ultimately impacted academic achievement in one urban district. Template analysis of 11 semistructured interviews and observation notes employed the positive psychology well-being theoretical construct, PERMA(H). Illuminated was the administrations' focused attention to student attendance, engagement, and well-being preceded academic achievement gains. The narratives addressing identified non-academic barriers informed six key findings. The findings are supported by 19 specific administrator activities that could be useful for other urban administrators desiring to address non-academic barriers to improve academic achievement.