Introduction Programs supporting adolescent parents have been shown to increase socioeconomic opportunities and promote healthy child development for young families, but retaining young parents is challenging. The Massachusetts Pregnant and Parenting Teen Initiative (MPPTI) offers case management and linkages to community and clinical services to young families. We examine engagement strategies identified by MPPTI participants and staff members in relation to participant retention by program site to identify potential strategies for increasing program engagement. Methods We employed a mixed-methods approach incorporating quantitative data on program participant characteristics and program retention by site with qualitative data from staff and participant interviews and focus groups. Results Key program engagement strategies identified by both MPPTI staff and youth participants were social-emotional supports, staffing model, and concrete supports. We found significant differences in program retention by site; the two sites with the highest levels of program retention offered all engagement strategies identified. Discussion Quantitative data on program retention coupled with qualitative data from staff and youth interviews suggests that in our program, there may be an association between the engagement strategies identified and levels of program retention.