The psychiatrist is often required to intervene in situations where difficulties are not determined by the severity of clinical symptomatology per se, but rather, more generally, by the complexity of the psychopathological picture that may engender difficulties for diagnostic framing, which may not always be shared by diagnosticians. Such diagnostic difficulty determines a further complication, i.e., the identification of the most appropriate drug treatment, especially where there is a lack of guidelines or where there is comorbidity between the various DSMIV axes, as for example, between personality or organic disorders. A brief description of clinical cases taken from everyday outpatient practice may provide hints for discussion and suggest common etiopathogenetic hypotheses for apparently distant conditions.