Ludwig von Bertalanffy was one of the main creators of the internationally well known “General System Theory”, a supradisciplinary approach that allows for better understanding of living beings as nonlinear complex adaptive self-organizing systems. Following his ideas we organized a first workshop in March on basics of “Organismal Systems Medicine” (OSM) that is a developmental biological top-down approach compared to the bottom-up approach of Molecular Systems Medicine (MSM). OSM highlights the principle “structure follows function” versus traditional “function follows structure” but is integrative in theorizing. The participants, before all well-known Uri Alon (Tel Aviv), tried to build bridges between clinical findings, experimental laboratory data and mathematical modeling. Focus was endocrinology and its circuitry links to the brain and to metabolism regulating organs and molecular processes especially regarding diabetes. In consequence, we organize this second workshop in order to discuss comorbidity, namely that of diabetes and depression, from a multi-level cyber-systemic viewpoint that aims to connect conceptually mind, brain, endocrine structures and the immune system on the basis of emorical evidence.