This study explores the stability of attachment security and representations from infancy to early adulthood in a sample chosen originally for poverty and high risk for poor developmental outcomes. Participants for this study were 57 young adults who are part of an ongoing prospective study of development and adaptation in a high-risk sample. Attachment was assessed during infancy by using the Ainsworth Strange Situation (Ainsworth & Wittig) and at age 19 by using the Berkeley Adult Attachment Interview (George, Kaplan, & Main). Possible correlates of continuity and discontinuity in attachment were drawn from assessments of the participants and their mothers over the course of the study. Results provided no evidence for significant continuity between infant and adult attachment in this sample, with many participants transitioning to insecurity. The evidence, however, indicated that there might be lawful discontinuity. Analyses of correlates of continuity and discontinuity in attachment classification from infancy to adulthood indicated that the continuous and discontinuous groups were differentiated on the basis of child maltreatment, maternal depression, and family functioning in early adolescence. These results provide evidence that although attachment has been found to be stable over time in other samples, attachment representations are vulnerable to difficult and chaotic life experiences.