Multiple placement changes disrupt continuity in caregiving and undermine well-being in children in child welfare. This study conducted secondary data analysis of a randomized controlled trial to examine whether a relationship-based intervention, Promoting First Relationships^© (PFR), reduced risk for a maladaptive cascade from placement instability to less secure attachment to elevated externalizing problems. Participants included caregivers (birth or foster/kin) of toddlers (10–24 months) recently transitioned to their care because of child welfare placement decisions. Although main effects of PFR on security and externalizing problems were not previously observed, this study’s results revealed that PFR attenuated the association between multiple placement changes (baseline) and less security (postintervention) and that the indirect effect of placement instability on greater externalizing problems (6-month follow-up) via less security was evident only in toddlers in the comparison condition. These findings shed light on how a history of multiple caregiver changes may influence toddlers’ risk for poor adjustment in subsequent placements, and the promise of supporting caregivers through a parenting intervention to prevent such risk.