Handwritten texts carry significant information, extending beyond the meaning of their words. Modern neurology, for example, benefits from the interpretation of the graphic features of writing and drawing for the diagnosis and monitoring of diseases and disorders. This article examines how handwriting analysis can be used, and has been used historically, as a methodological tool for the assessment of medical conditions and how this enhances our understanding of historical contexts of writing. We analyze handwritten material, writing tests and letters, from patients in an early 20th-century psychiatric hospital in southern Germany (Irsee/Kaufbeuren). In this institution, early psychiatrists assessed handwriting features, providing us novel insights into the earliest practices of psychiatric handwriting analysis, which can be connected to Berkenkotter's research on medical admission records. We finally consider the degree to which historical handwriting bears semiotic potential to explain the psychological state and personality of a writer, and how future research in written communication should approach these sources.