Late antique monks were constantly besieged by demons. This article seeks to gain an insight into the reality behind monastic accounts of this demonically-induced psychological state, characterized by an uncontrollable preoccupation with demonically-inspired thoughts. This distressful experience is depicted in early monastic sources by using Greek verbs expressing “to besiege”, which have been rendered into Latin as obsidere (to besiege) – the etymological root of “obsession” in modern usage. A juxtaposition of modern accounts of obsession and monastic accounts of the besieged mind points to striking similarities in the symptoms – similarities which, I argue, are not accidental. Rather, the internalized interpretation of the siege enabled monastic writers to cope with questions regarding the aetiology of obsession-like symptoms. Cognitive research of obsession helps to account for the prevalence of this demonically-induced psychological state in monastic sources. Thereby it underscores the sophistication of monastic psychology cum demonology, which developed its own representation of the human mind and its operations.