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In this paper we present the results of a study that demonstrates the ability of an Intelligent Tutoring System (ITS) to increase parental engagement in student learning. We developed a parent notification feature for the web-based ASSISTment ITS that allows parents to log into their own accounts and access detailed data about their students’ performance. We then invited parents from a local middle school to create accounts and answer a survey assessing how engaged they felt they were in their students’ education. We ran a 60 day study during which we sent messages home to parents regarding what their students were studying in class and how they were performing. After having them take a post-survey, we found that parents felt significantly more engaged in their students’ education. Additionally, the messages significantly increased how frequently parents logged in to check reports on their students’ performance data using the ASSISTment system. Qualitative feedback from both parents and teachers was extremely positive.