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This article explores an adolescent's use of technology to develop friendships, express autonomy, separate from parents, and explore sexuality. At times, electronic communication threatened to overwhelm the therapeutic space at the same time it promoted the therapeutic alliance and resulted in developmental growth in the adolescent. The handling of technology within the family revealed dynamics of control, agency, and enmeshment. Clinical material illustrates the complexity of using a variety of modes of communication within the therapeutic space to facilitate psychic change, develop relationships, and accomplish separation-individuation from parents.