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The COVID-19 crisis has provided unique opportunities for the expansion of telepsychotherapy services. To date, the extant literature on telepsychotherapy has not included many strategies for effective telepsychotherapy with youth and families. This paper examines the evolution of a play psychotherapy case conducted fully online amidst the COVID-19 pandemic in 2020. A review of the telepsychotherapy literature is provided and multiple aspects of online psychotherapy are explored within the context of a completed, online psychotherapy treatment with one eight-year-old girl with externalizing symptoms. This case study is the first start-to-finish online case of Regulation Focused Psychotherapy for Children, and to our knowledge one of the few known case studies of a completed, fully online, child psychotherapy case. Clinical vignettes illustrate how the therapist’s interpretation of the child’s defenses within an online modality allowed the child to progress in her ability to tolerate painful emotions. In addition, countertransference reactions of a novice therapist, treating her first psychotherapy patient, are highlighted. This unique case study provides support for the value of an online, play-based treatment for children with behavioral issues and their families.