Schools are increasingly bolstering student character strengths to promote academic success and well-being. Schools’ character-promotion efforts would benefit from involving students’ caregivers. Online resources may be an accessible way to engage students’ families, but further research is needed to maximize accessibility and engagement. A brief character strengths program was developed and integrated within online accounts accessed by parents of kindergarten students. Content analysis of parent focus groups (N = 14, 86% women) indicated that access to and engagement with the program was improved by several factors, including visuals, intuitive navigation, strength-based content, and school-based recruitment. Content analysis of caregivers’ (N = 54, 91% women, Mage = 36.52, SDage = 4.40) responses to the program’s reflection questions indicated that parents prefer highly applicable content, particularly information about noticing and developing character strengths in their child. Finally, exploratory descriptive statistics indicated that single parents, fathers, and parents of racial minority children were less likely to engage with the program which alludes to the additional barriers faced by these socio-demographic groups. The results provide specific suggestions for involving parents in school-based character promotion efforts, as well as highlight the importance of additional research to better understand the needs of diverse families.Supplementary InformationThe online version contains supplementary material available at 10.1007/s41042-022-00072-4.