This chapter takes as its point of departure the complementary accounts by two of the pioneers in the study of marginalia, Heather Jackson and William Sherman, of the ways in which the age-old practice of writing in books has been disparaged and condemned. It aims to explore the particularities of that discourse of condemnation in Australia in the nineteenth- and twentieth-centuries, using the resources of Trove, a comprehensive database of Australian metropolitan and provincial newspapers, to illustrate its tendency to articulate conflicts and anxieties around class, gender and national politics in the guise of moral disapproval and aesthetic distaste. However, taking its cue from personal reflections by Joan Didion, Patricia Meyer Spacks, and others, the chapter also seeks to show the enduring ambivalence of this condemnation in its own terms, an ambivalence that permitted various forms of annotation to retain their popularity as pedagogical instruments, especially for the study of literature, until well into the second half of last century. In tandem with that, it illustrates the continuing power of annotations to provide unpredictable insights into the education process, and occasionally to function for individuals as a means of intellectual self-recovery and ethical self-scrutiny.