Students need digital learning resources that will benefit their learning process, and educators need tools that provide meaningful data insights and can be integrated into their teaching practice. Courseware as a learning resource is designed based on learning science principles to optimize the learning process for students. However, it is also well-known that digital resources do not get optimum engagement on their own. The instructor’s approach for implementation can have a sizable impact on student engagement—and ultimately—on outcomes. In this paper, we will compare two courses run in the spring of 2020 and spring of 2021. The courseware used here was created initially by artificial intelligence and automatic question generation and further enhanced with adaptivity and assessments by the instructor and instructional designer. The instructor taught both classes online using the same courseware, but made changes to how she implemented it. We will compare data from both sections to understand how these implementation changes impacted students—from platform engagement and learning data to student final exam data. Results show that the instructor’s implementation changes increased student use of the courseware throughout the semester, and also increased exam scores. This direct comparison showcases the importance of instructor choices when incorporating digital resources into the classroom and provides a set of successful implementation practices for other educators to model in the future. In a time of significant change in education, it is more important than ever to better understand how technology and teaching practice can work together to help students be successful.