Identity and diversity permeate teaching and learning. Technology-mediated learning environment designs are infused with cultural values, norms, and assumptions. In addition, age-related diversity mediates interactions, learning, perceptions of instruction, self-regulation, and experience with technology. Individual instructors and/or instructional designers are both cultural insiders and cultural outsiders to diverse groups of online learners. Learning difficulties are likely to arise when underlying pedagogical values, norms, and epistemologies in an online learning setting are culturally inappropriate or ineffective for a learner group. Instructors and learners are usually unaware of how identity and diversity manifest in teaching and learning, and hence experiencing challenges in negotiating academic norms.