Like other adult education providers such as the Workers' Educational Association, the educational settlement movement was beset with political controversy during the 1920s. This article considers the relationship between the Educational Settlements Association (ESA) and its affiliated institutions, relating these to the competing political traditions that were represented in the movement. In particular, there were differences between the Liberal members of the ESA executive committee and the Labour-supporting settlement wardens, many of whom were active in local politics. The article considers disputes concerning the funding of settlements, the political activities of wardens, and student representation within the institutions. It shows that, although wardens campaigned for greater democracy within the ESA, they resisted democratic control of their own settlements. The article focuses on the settlements in Sheffield and Walthamstow, and the John Woolman Settlement in Islington. It is based on the records of these settlements, and of the ESA itself. (Contains 150 footnotes.)