This exploratory study addresses the challenge of declining family engagement at the critical transition to high school. We use data from a survey of schools to examine whether and how middle grades and high schools engage families when their students transition to high school. Findings indicate that there is a significant negative relationship between the proportion of students who struggle during the first year of high school and the quality of high school outreach to families in the transition period, even after school poverty level is controlled. The study also shows that, even among a group of schools actively implementing a systematic approach to engage families, considerable work remains to enable educators to engage families during the critical transition to high school in ways that help improve student outcomes in the ninth grade.