The rapid dissemination of digital technology has fundamentally changed our students in the Caribbean. Some of these students have spent their lives surrounded by computers, video games, digital cameras, text messaging, and cell phones. In contrast, these students are enrolled in programmes offered by universities in the Caribbean which are taught and managed by individuals who did not experience the pervasive digital technology culture when they were growing up, as is the norm for these students. Information technology (IT) infrastructure is being established as universities invest in them to support the growing demand for IT from students, faculty, and other staff. Administrators are constantly being challenged to develop institutional plans for IT that will support research, teaching, and learning. In spite of these investments, there is a gap between the promise and the reality of innovative instructional and learning practices in many universities. This paper identifies the challenges posed by the technology divide between students and administrators, and proposes management strategies that administrators of Caribbean universities can use to address the challenges driving the technocultural gap in higher education.