This empirical mixed methods study examines educators' understandings of student risk factors. The research was conducted in a Title 1 combination middle high school in the Florida panhandle that had been open for three years and had received a grade of F school in each of these years. In Florida, schools are graded according to the Florida Comprehensive Assessment Test (FCAT), which includes the following categories: achievement in reading, math, science, and writing, as well as annual learning gains in reading and mathematics. Schools can also be awarded bonus points if "at least 50% of their 11th and 12th grade students pass the FCAT retake in reading and math". Even with the addition of remedial scores, the school where this research was conducted has been designated as failing every year. The question, which guided the research was: how do educators in this failing school understand risk as it impacts on student achievement? This study identifies individual, family, and community factors as well as school policies and practices that place students at risk. It expands the existing knowledge base related to school improvement and is important in the United States at a time when a focus on narrowing the achievement gap in schools is at the forefront of research and practice. This work also furthers discussions regarding hegemonic policies and practices of schooling and how entrenched deficit discourses, including conceptions of students at-risk, negatively impact on students from minoritized communities. The findings show a commitment on the part of individual educators to reduce risk and increase life chances for students in this school. Unfortunately, these random acts were not supported at institutional levels. Federal, state, and district policies and practices create a climate or risk wherein it is amazing that these teachers and administrators persevere or that any student in this school community attains academic success. The narrow curricular and testing focus and existing salary disparity combined with administrator turnover contribute to the district's difficulties in attracting enough strong educators to change the deficit thinking that pervades this school. While higher pay does not automatically translate into better teaching practices, it could serve to create a larger pool of applicants for teaching and administrative positions in the district. (Contains 1 table.)