The University of Sydney has offered some form of organised adult education since the late 19th century. In 1914, that provision was formalised through the establishment of a Department of Tutorial Classes, the appointment of a Director, and a partnership with the Workers' Educational Association (WEA). Right from that time, however, there was ambivalence and sometimes direct opposition to the role and sometimes to the existence of the department. As a result, successive directors of the department had to tread a fine line in balancing the expectations of the university with their passion for extending the academy into the adult community, while also satisfying the demands of the WEA. This paper reviews the period of three directorships of the Department of Tutorial Classes, between 1919 and 1963, and argues that the liberal adult education approach adopted by the university from its earliest days was sustained over those 45 years mainly because ongoing disagreement within the university about the purpose of the department and the status of the director, as well as continuing external pressure from the WEA, ensured that the status quo prevailed, even when there were innovative adult education developments elsewhere, and opportunities for change presented themselves.