This case study explored the effectiveness of telementoring as a vehicle for preservice teachers to hone skills in the teaching of writing, to establish a mentoring relationship with urban high school students, and to help struggling writers improve writing skills necessary for student achievement. Inherent in this research was the goal to develop a collaborative model between the university and the high school for using technology to improve “at-risk” urban students’ skills in writing. Additionally, the research allowed preservice teachers to learn about themselves as evolving teachers as they broached some of the difficulties of teaching writing to academically diverse students and learned about the scarcity of resources and difficult realities that exist for urban students.