This report examines the implementation of the first year of the Pennsylvania High School Coaching Initiative. Funded by the Annenberg Foundation, it is an on-site professional development initiative that employs instructional coaches using Penn Literacy Framework in an attempt to improve the level of teacher instruction in districts across the state. Using a mixed methods approach, the report draws from both quantitative and qualitative data as it describes the roles of the partner organizations involved, the hiring process of coaches and their training, the initial implementation of the initiative in schools across the state, the successes and challenges from Year One, and discusses lessons and recommendations for Year Two. Findings suggest that there are specific enabling conditions--supportive leadership, time, etc.--that are necessary for coaching to work and design infrastructures and interventions aimed at creating those conditions. Appended are: (1) Participating Districts and Schools; and (2) Methodology. (Contains 13 figures and 30 footnotes.)