There is a paucity of research on the diagnosis of dissociative disorders in children. Most children are misdiagnosed with more common mental disorders with similar symptoms. Earlier recognition of dissociative disorders can save years of pain, suffering, and cost. This qualitative collective case study examined the process of diagnosing dissociation in two children under the ages of 12 at the beginning of treatment. A concurrent focus on the training and development of the therapist/researcher is included. Archival data including progress notes, psychotherapy notes, assessments, correspondence, legal documents, school records, and medical records were analyzed using within-case and cross-case analyses to identify individual and common themes that may expedite the diagnosis of dissociative disorders in children. The narrative presentation of a qualitative study with its thick, rich description may increase the understanding of clinicians with little or no experience and help them to differentiate these disorders from other disorders with overlapping symptoms. Factors that impeded and advanced the recognition of dissociative disorders were identified. Clinical findings underscore the role of knowledge and training, experience, and consultation in the diagnosis of dissociative disorders.