Psychosomatic disorders represent a therapeutic conundrum. Despite compelling evidence to suggest the integrity of mind and body, humans are famously prone to experiencing them as separate. This paper explores the scientific challenges posed by psychosomatic disorders and how changing cultural notions contribute to their perplexing presentations. Excerpts of cases from patients with chronic pelvic pain, chronic fatigue, and a factitious disorder are presented as examples of the challenges that these patients pose in analysis. An explanatory model of mind/body interaction based on early maternal-infant interactions and the placebo response complex is proposed as the basis for how psychosomatic pathologies may develop. Finally, therapeutic approaches to the psychological treatment of patients with psychosomatic issues are considered.