This article explores the complex contexts and relationships that enabled student civil rights advocates to emerge at Howard University in the 1930s and 1940s. Such histories are valuable given their realistic portrayal of the daily challenges, interpersonal collisions, collaborations, and organizational positioning that made some human rights victories possible and delayed or stopped others. Further, they show how student leadership in pursuit of civil rights could exert pressure on institutional leaders to continue to define the mission and role of a prominent historically black university and the education it provided. The civil rights advocacy of Howard University students in the 1930s and 1940s exposed the hardships of achieving progress against Jim Crow systems of prejudice given the competing interests and concerns that existed among the advocates themselves. Few things came easily as students and administrators collided over direct action techniques, adverse publicity, the politics of institutional funding, and the purposes of education for black students.