This article can be broken down into two parts, perhaps somewhat unequally as far as its orientation is concerned. In the first part, the author takes the reader on a kind of exploration of the history of moral education, a subject which, at first glance and from the perspective of the years he spent studying educational historiography, appears to be rather undeveloped terrain. Since the piece is related to the awarding of the Comenius Medal, Comenius himself already provides a good starting point for this round of studies. As in the case of Herbart, another classic within the canon of educational history, Comenius held the opinion that morality plays a key role in upbringing of young people, which became increasingly scintillating in appearance from the Enlightenment onwards. For in a well-regulated society, it was by means of upbringing and education that individual freedom could be created. However, in the course of the 20th century and to the shame of humanity, people were forced to witness how the idea that people and society could be shaped by social engineering could equally give rise to a lack of freedom, as the aberrations of Nazism, fascism and ultimately Marxism-Leninism unequivocally demonstrated. So can such “reversals” of modern-day thought ultimately teach us any overall lessons about the content, manner and results with which moral curricula are imposed? Or must we first set out to identify the “abnormal” cases that society first branded as such and only subsequently extract those lessons? In other words, can extraordinary situations and events teach us something about the everyday reality of moral education as manifested in the so-called “civilising offensive” that took place from the end of the 18th century onwards? As far as the Low Countries are concerned, the author is, for that matter, setting foot on familiar ground. By utilising previous research on Belgium, Flanders and the (Belgian) Congo, the second part of the article wastes no time in examining what moral education meant in more specific terms in the 20th century. In that regard, the focus not only lies on contextualising the insights and questions raised by the first part, as a “tour d’horizon”, but equally on analysing them in greater depth. After all, the author’s years of research already provide three interesting points of reference: 1) the strong continuity of the patronising perspective; 2) the problematic nature of thinking about educational innovations and didactic innovations in binary terms, such as “old” and “new”, and 3) the lack of a straightforward link between parenting and educational goals on the one hand and their results and effects (including and especially in the long term) on the other. Which leads inevitably to the conclusion that education, important as it is, must not be overestimated. Nor should history for that matter. Perhaps both are nothing more than an opportunity to partake of a meaningful encounter that may be effective, but whose outcome one can never be sure of. Which in turn does not take away from the fact that we must still place our hopes on it. For hope is probably the most positive thing that human beings carry within them, just as Comenius himself proved in his lifetime, by the way.