Teacher retention has become a great challenge for schools and school administrators throughout the United States. Large urban districts are particularly affected by this phenomenon due to the loss of both new and experienced teachers. Due to the importance of this issue, there is a large amount of empirical literature that explores why teachers choose to leave the profession and what can be done to induce them to stay. This study explored whether there are additional factors that may not have been addressed such as assessment policy, alternative teaching programs, and local context. It also explored the importance of these factors on teacher retention using data from interviews and focus groups of 6th, 7th, and 8th-grade middle school teachers in a large urban fringe school district in Maryland. It is hoped that this research will provide information school districts can use to understand how assessment policy affects teachers' feelings of disenfranchisement, and; incorporates teacher input in developing strategies to support and retain highly qualified, highly effective teachers.