This study examines paternal and maternal sensitivity as predictors of toddlers' attachment security in two naturalistic contexts. Seventy-three mostly White middle-class families participated between 2015 and 2019 when children (49.3% girls) were approximately 29.48 months old. Each child-parent dyad completed a home and playground visit. Findings revealed paternal and maternal sensitivity were significantly associated at home and marginally at the playground. Paternal sensitivity was only predictive of security to the father at the playground, showing a medium effect, while small effects of maternal sensitivity on security to the mother were found in both contexts. Cross-parent contributions to security were small and limited to the playground. The need to consider the greater ecology of child-parent relationships and suggestions for larger-scale research are discussed.