Digital technologies are quickly being combined with and replacing teacher curriculums and student resource tools. This is particularly true with advances in digital textbooks as it provides a medium for opportunity and growth in the nature of the textbook as it pertains to students in the classroom. Although great strides have been taken in intelligent tutoring systems personalized toward a student's needs there seems to be an overall disconnect between student needs in the classroom in not utilizing or adopting these technologies. In this paper I provide both conflicting and comparable needs of teachers and students surrounding the textbook to reveal the costs and benefits associated with technology adoption. Through 4 teacher interviews and 4 participatory prototyping sessions I found that students and teachers desire the following elements in technology: 1) Collaboration 2) Synchronicity 3) Adaptive 4) Automation. I discuss the implications of implementing such features and how they could be applied in integrated Q&A system to encourage collaborative learning.