With increasing class sizes, faculty have increasingly been using online homework software (OHS) and in-person discussion groups as the classroom evolves. We sought to determine the effect of online homework software and in-person discussion groups on student engagement. Specifically, we posited that expectations influence this relationship, and we applied Expectation Disconfirmation Theory (EDT) to determine whether a student's expectations about discussion groups or OHS impacts Student Engagement. Moreover, with EDT, we assessed whether these impacts are direct. Our results indicate that if instructors facilitate the development of expectations when students work in groups in a class, the student's level of group satisfaction in addition to engagement in the course will be positively influenced. However, the findings indicate that OHS exerts differing effects. When instructors focus on developing realistic expectations about the OHS used in class they will achieve greater satisfaction with the technology. This satisfaction with the technology will then lead to student engagement in the course. This exploratory study, in spite of a few limitations, demonstrates the importance of managing expectations in the classroom, and its impact on current educational tools. The study also identifies additional research questions on expectation management relating to student engagement that would reduce the impact of these limitations.