In response to a thirty-year pattern of elevated high school dropout rates and a multi-generational disengagement from traditional school-based literacy practices among urban community members, the project on which this article reports asked a group of city students to document photographically what they perceived as the purposes of, impediments to, and supports for their school success. Grounded in "New Literacy" and visual sociology traditions, this examination utilized as research tools image-based mechanisms with which city students were already proficient. Findings drawn from three versions of this project conducted with nearly 100 youth suggest that English language arts teachers committed to engaging their students in effective writing instruction might focus more on the use of arts-based methods and open-ended questions as "ways in" to writing, on sharing these youths' writing efforts with broader--and younger--community members, and on more 1:1 student/teacher interactions that occur over extended periods of time. (Contains 4 figures.)