This chapter acquaints the reader with key concepts associated with learner engagement by examining the user interface from cognitive, semiotic, psychological, artistic and pedagogical perspectives. Technology affords educators with a new way to present course content that is no longer text only, paper constrained, linearly organized and visually flat. Engaged learning can borrow from the interactive and community-based activities prevalent on the Internet. The use of gaming, role playing, blogging, instant messaging and chat coupled with multimedia modalities that address multiple learning styles had the capacity to stimulate today’s technology savvy learners. By employing these familiar methodologies to learning, educators can better meet the needs of a new student demographic that has grown up with computers, is predominately visually orientated, watches rather than listens to music on MTV, uses Google as a key reference tool, shops online and accesses news through 24/7 online streaming feeds. These students expect to take part in experimental and authentic learning in unconventional and engaging ways. However, new ways of learning require new teaching methodologies. The traditional forms of teaching do not transition well to the engaging online environment. The authors, using a three-phase model as a foundation for creating engaging user interfaces, will explore the cognitive and visual elements of effective interface design that engage learners through intuitive and direct interaction. By deconstructing a series of educational interfaces that are functional, usable, communicative, and aesthetically appropriate, readers will leaner to identify the visual and cognitive demands of a knowledge domain that creates engaging, interactive results.