This study explored the applicability of family drawings as a tool to estimate attachment security in a sample of Japanese six-year-olds (N = 47), applying Kaplan and Main's (1986) Family Drawing system. Maternal secure/insecure attachment status judged by the Adult Attachment Interview predicted family drawings' secure/insecure distinction produced by Japanese six-year-olds. However, insecure Japanese drawings took forms not seen in the original Berkeley drawings, such as a lineup of faces alone. Further examination of the Japanese children's drawings using global rating scales (Fury, Carlson, & Sroufe, 1997) yielded significant gender differences, rarely reported in the attachment literature, with girls scoring higher in scales that predict attachment security and boys scoring higher in scales that predict attachment insecurity. However, attachment security, as captured in the drawings, was not related to attachment security, observed behaviorally using Main and Cassidy's (1988) sixth-year reunion system. Implications of the findings are discussed in light of measurements, gender, and culture.