Margaret and Annie O’Connor were second-generation Irish-Australians who lived in Waterloo, New South Wales, over a century ago. Scorned by the judiciary as ‘most undesirable’ women, Margaret and Annie’s so-called legal and moral ‘crimes’ included smoking opium, drunkenness, swearing, being tattooed, doing sex-work, and consorting with Chinese men. This presentation offers insights into the lives of women who, like Margaret and Annie, were criminalised by poverty, and of new ways to write about them.