The purpose of this study is to map the medicalisation of learning difficulties in the remote and mountainous areas in Chania Prefecture, Crete, when pupils are referred to Diagnostic Institutes to be assessed and possibly receive a learning difficulty diagnosis. It provides evidence on the fact that the learning difficulties identification procedure tends to be individually oriented and to neglect contextual dimensions, as well as the interactions between them, particularly in light of the consequences of the socioeconomic crisis in Greece. The remote and mountainous areas in Chania Prefecture, Crete, serve as a case study. Educational documents, archives, newspapers, and laws are examined, and six semi-structured interviews are conducted and analysed. The analysis yields two core themes: a. Exaggerated diagnoses: a compensatory tool and b. The emergence of the environment of the contexts: the impacts of the socioeconomic crisis. As an outcome of the analysis, it occurs that the medicalisation of learning difficulties appears to impose an obstacle to the detection of the deeper systemic, social, and political causes of these difficulties. It may also fail to sufficiently address the needs of the involved parts, namely pupils, parents, and schools. Given the implications arising from the study that indicate the systemic nature and influences of learning difficulties, the necessity for a transition towards a bioecological approach is discussed.