The purpose of this multiple intrinsic case study was to describe how Northeastern United States middle school teachers and students engaged with a new automated writing evaluation tool used to score and provide feedback on extended essay assignments to improve teaching and learning writing. Richard Elmore's (1993) instructional core framework is the theory guiding this study. The study's central research question is: How do public and private middle school students and teachers engage with the automated writing evaluation program WisdomK12? The study leveraged an intrinsic case study design and triangulated data from educational artifacts, individual interviews, and questionnaires. Results indicated that students and teachers found WisdomK12 to save time, provide relevant, encouraging, and authentic feedback, and inspire them to write more. Implications and future research are discussed.