Reengagement is the least obvious of Cultural Maturity’s defining themes and also the most readily misunderstood. Culturally mature perspective requires us to reconnect with sensibilities that knew their strongest manifestations in earlier cultural times. All of Cultural Maturity’s defining limits can be thought of as aspects of single more fundamental limit: that of continuing on as we have. Going back would lead us just as far astray. But Cultural Maturity does predict that the past in times ahead will gain a new depth of significance. A major portion of what gives us the experience we call maturity—in systems of any sort—derives from a new, more conscious and deeper relationship to aspects of ourselves more readily accessed in times past. This reconnecting follows from the way formative processes of all sorts inherently work. Deep and accurate appreciation for Reengagement is necessary if the concept of Cultural Maturity is to make real sense and if claims of hope are to have a sound basis.