Today, many principals are assigned to struggling schools with the mandate to quickly change the academic trajectory of the students. Interviews were conducted to gain an understanding of how principals and core teachers working at rural middle schools under chronic academic stress perceived the increased academic expectations at their schools. Three key findings were revealed: (a) There were misaligned principal and teacher interpretations of efforts to improve the school; (b) there tended to be an ongoing focus on what was wrong with the school; and (c) principals felt they were alone in the process. A discussion of these findings is provided