In 2000, Sara E. Shea and co-authors published "Pathology in the Hundred Acre Wood: A neurodevelopmental perspective on A.A. Milne" in the Canadian Medical Association Journal. That article gave provisional "diagnoses" to Christopher Robin and his companions under the then-current Diagnostic and Statistical Manual for Mental Disorders (DSM)-IV criteria. For example, Winnie-the-Pooh was diagnosed as suffering from ADHD (inattentive subtype) and Obsessive Compulsive Disorder (OCD), while Piglet's condition fell under the heading of Generalized Anxiety Disorder. This case study is based on that article in order to make discussion of difficult topics more accessible and less threatening without minimizing their importance and seriousness. Students in abnormal psychology or other psychology classes will use various explanatory models including behavioral, biological, cognitive, psychodynamic, humanistic-existential, and sociocultural to discuss possible contributing factors and treatment options (appropriate to an undergraduate class) for these and other inhabitants of the forest. The case also provides resources for students to discuss the 2013 transition from the DSM-IV to the DSM-5, and the changes in the diagnostic system inherent in the new edition.