This Clinical Case Conference discusses the use of Circle of Security, a new psychotherapeutic intervention that has a growing evidence base, as applied to a serious attachment disturbance in a mother and her toddler. Circle of Security is designed to enhance reflective functioning and increase parents’ awareness of the needs of their young child. The case presentation is of a mother and her 18-month-old toddler. Videotapes of key moments illustrate how the use of video rich psychotherapy may address serious attachment disturbances between mother and child.