This chapter focuses on psychiatric-physical comorbidity education and trainee needs. It notes a threefold challenge of poor psychiatric education in general doctors, atrophied psychiatric physical health skills, and self-selected disinclination of psychiatrists toward comorbidity. It particularly explores contributory historical factors. Early psychiatry was somatically inclusive, but treatment-moral shifted this, before supplantation by biological eclecticism. Educational programs were dominated by administratively focused superintendents. Germanic models prioritized scientific rigor over clinical skills. Flexner helped integrate sciences into medical teaching, but psychiatry lagged. The sequential rise of neurology and then consultation-liaison psychiatry sequestered physical comorbidities from the generalist psychiatrist. Psychoanalytic dominance precipitated a split whereby some eschewed somatic treatments, while others intervened egregiously, reinforcing a psychiatric hesitancy to involve itself in the physical. Difficulties in teaching psychotherapy exacerbated poor undergraduate understanding. Psychiatrists deskilled in physical health, only reskilling ad hoc for medication monitoring. In modern times, supervision struggles when supervisors lack the physical health skills they are expected to teach, with re-accreditation insufficiently incentivizing comorbidity training. Hierarchicalism impedes junior doctors learning comorbidities and contributes to a culture of silence and potential humiliation. Recommendations for teaching comorbidities include not worsening the trainee’s situation, multimodal teaching (including neurodiversity-friendly options), formal education training, disinformation management, discretely taught interventions, and destigmatization.