This article discusses the use of the telephone for psychotherapy and applies basic tenets of attachment theory and research on infant development to understand the therapy process. Clinical case examples of four models of attachment (“secure,” “insecure ambivalent,” “insecure avoidant,” “disorganized”) illustrate diverse patient capacities to use the telephone during a planned 10-week break from ongoing, in-person treatment. It is suggested that telephone therapy may be variously effective based on the attachment system that becomes activated due to the separation, and patients with insecure avoidant or disorganized attachment patterns may have more difficulty managing the alternative treatment modality.