Until the 1950s, many teachers in Saskatchewan still taught in one-room schools located within farming communities and, in these rural settings, were under close scrutiny by farm men, farm women and their children. While focusing on the gendered constraints at play, this paper explores how women teachers lived with, negotiated and challenged these prescribed expectations. I examine the regulation of rural women teachers by local farm families in their capacities as parents of school children, school trustees and landlords in the first half of the 20th century. I argue that the expectation to be a quiet and conforming female by community members, as enforced by the total discretion over firing and rehiring, made it difficult for rural women teachers to assert autonomy and agency. For those women who attempted to deviate from the standards of this time, the visibility of their activities constrained their latitude of departure and left them vulnerable to disciplinary measures. First hand accounts from 200 women, who taught in rural Saskatchewan in the first half of the 20th century, provide the basis for this analysis