The first part of this report looks closely at the background, structure, and function of the DESE in an attempt to understand how the agency has operated, how it currently operates, and what challenges, if any, the structure and operation of DESE pose for its ability to effectively exercise its increased authority. The second part recounts the recent history of the Department, especially its role in implementing the first wave of education reform, which came in the form of the 1993 Massachusetts Education Reform Act. In doing so, this work uncovers some of DESE’s strengths and weaknesses in an attempt to highlight potential obstacles to successfully implementing the second wave of reform.