This chapter examines the second and third years of Wednesdays in Mississippi (WIMS), an interracial, interfaith civil rights organization sponsored by the National Council of Negro Women (NCNW). In the summer of 1965, around fifty black and white, Protestant, Jewish, and Catholic women returned to Mississippi to help with Head Start, the newly formed War on Poverty program. Despite increased activist calls for more participation and leadership from the grassroots and poor, WIMS continued to promote its elite pedigree by highlighting its members' expertise in teaching, social work, librarianship, and child development. In 1966, WIMS began to shift its focus to bridge building in the North, promoting the liberal strategy of interracial and interfaith conversations as a method to create personal change and combat racial discrimination. However, by 1966, WIMS leaders began to realize the limitations of such a strategy when they were rebuffed in both Mississippi and Boston.