The academia-industry gap in undergraduate CS education has been a well recognized problem over the past two decades. Many papers have identified this gap or proposed novel solutions to parts of it. Yet, recent studies found the gap persists. This dissertation explores various possible reasons that could lie behind the persistence of this gap. We uncover that the majority of CS faculty support including more industry-relevant content in their courses. Faculty do however experience a skills, resources and awareness gap which forms a barrier to making their courses more relevant to industry practice. Moreover, we find that these barriers are experienced by CS faculty at top universities world-wide. Furthermore, many of the efforts to close the gap do not adequately address known barriers to adoption and barriers encountered by faculty. Additionally, one concern raised by some faculty is that students may not be learning the skills that we are teaching. These faculty are partially correct as we find evidence indicating that the average student proficiency with prerequisite materials may not be fully aligned with instructor expectations. Moreover, a different study indicates there are performance disparities between several subpopulations of students. However, we also find evidence that indicates that students on average continue to improve their understanding of CS fundamentals as they progress through their program, indicating that students on average do appear to learn the materials that we teach.