This essay examines late-antebellum portrayals of Irish servant women in popular culture and the Pennsylvania Abolition Society’s (PAS) wartime correspondence with northern employers eager to obtain access to southern freedpeople. In these sources, white northerners filtered their characterizations of women’s bodies and behaviors through ideologies of gender and race to create submissive and transgressive social types representing ideal and less-than-ideal workers. These declarations about workers, yoked to the northern argument that emancipation was both an act of benevolence and a period of necessary instruction for black southerners in the habits and practices of wage labor, propelled northern benevolent associations, armies, and the state to forge a transportation network that they hoped would ensure the flow of workers northward. This network proved short-lived, ultimately foundering on a lack of funding and employers’ and employees’ mutual disappointment with each other. And yet, because of their wartime cultural work, employers could pivot to a position of even greater strength over white and black workers in the political economy of wage labor.