This research uses a qualitative research approach, specifically a single-case study method, to explore the journey to school improvement of one struggling school district that is involved in year 2 of a 3-year turnaround plan. The single-case study method allows the researcher to use several data collection methods to build a picture of the improvement process. Interviews, observations, artifact collection, data analysis, journal writing, and the development of analytic memos comprise the broad spectrum of ways in which data were collected. This research explores the approach the district is taking and the role of the state of Massachusetts in the improvement process. The research takes place at a time when expectations for increased student achievement in Massachusetts, across the United States, and in numerous other countries throughout the world have taken on great importance. The stories are similar: factories have closed, production of goods has become automated or has moved to less expensive places in this global economy. Once prosperous cities and towns are now faced with school systems that need to address the needs of those students who come from low-income families with few resources at home, vast numbers of homeless students, and students from homes where English is not spoken and homes where parents are struggling to make ends meet. These demographics impact the schools, and with important services to offer and too little money to do it, these schools are often among the lowest performing schools in the area. This case study will examine the process the district is going through, the struggles of the participants, and the documentation of progress through the data generated. It will situate the case study in a city that has had poor student performance for many years. [This content is provided in the format of an e-book.]