Many school district leaders, high school administrators, and teachers--particularly those in urban areas--have struggled to reduce high school dropout rates but find themselves overwhelmed by the dimensions of the problem. Consider: Research has shown that lack of preparation in elementary and middle school, long before students reach high school, is a key factor affecting dropout rates once these students are in high school. Moreover, improving the quality of teaching and learning in high school has proven to be a very difficult arena in which to make substantial progress. These challenges are further compounded by budget constraints that limit organizational capacity and by high turnover in district leadership positions. Insofar as the average tenure for an urban superintendent is a little over two years, it is easier for others in the system to lay low and avoid major change initiatives. A series of "strategic initiatives" often supersede each other in sequence, rising up and then fading in importance one year to the next. There are, however, a few districts making notable progress towards reducing the number of dropouts and ensuring that students earn high school diplomas in a timely manner. One of these is the Portland, Oregon, public school system. This case study tells the story of how Portland Public Schools (PPS) began to have a positive impact in addressing the dropout problem over the course of one calendar year. In particular, it follows the district leaders' actions as they moved from data and decisions to implementation and results for those high school students most at risk of dropping out as they transitioned into the 9th grade. It is important to note that PPS's efforts to reduce its dropout rate are part of a larger strategy to transform high school education in Portland. Thus, this paper takes a step back to examine the context in which the district's leaders began their work and the overall, multi-faceted vision they articulated. From there, the case zeroes in on the specific efforts undertaken to reduce the number of high school dropouts. Finally, it assesses the progress PPS made in the first year of implementation, and in a sidebar, presents several take-away lessons--illuminated by Portland's experience--that other school leaders might find useful as they strive to reduce their own dropout rates. (Contains 1 table and 13 footnotes.)