In this study, we evaluated complex patterns of attachment discontinuity across time in 133 individuals from the Minnesota Study of Risk and Adaptation. In addition to individuals who were either insecure or secure across infancy, late adolescence, and adulthood (Stably Insecure and Stably Secure, respectively), we found three additional groups: Infant/Adolescent Secure, Infant/Adult Secure, and Infant-only Secure. Changes in attachment representations in these groups across time corresponded to stresses and supports in the socio-emotional context. The two groups classified as secure in adulthood (Stably Secure and Infant/Adult Secure) experienced more positive relationship-based outcomes than the other three groups. Our results (1) suggest that continuity may be a reflection of a stable social context as much as it is an artifact of early working models, and (2) illustrate “homeorhetic” pathways of development, in which not only the direction but the length of a developmental pathway can constrain future developmental trajectories.