Using a collaborative program evaluation of a bridge program at a state flagship university, the authors argue that contradictions in student perceptions of their literacy learning are endemic to the effects of the structure of urban schooling. Overcrowding and underfunding of particular schools, in contrast with successful academic magnet schools, result in an uneven playing field as college-bound students of color enter competitive programs. The authors argue that programs designed to enrich college-bound students' experiences cannot work in isolation: better university/public school partnerships need to be pursued in order to ensure that students from urban settings do not arrive at elite universities lacking skills in academic writing. (Contains 2 footnotes.)