With the current advancement in information and communication technology, incorporating the already pervasive handheld devices for learning and teaching has become a common theme. The application of handheld learning devices in a one-to-one learning environment may further inform a specific need for structuring a seamless learning framework, establishing a holistic didactic paradigm, and directing future development. Within this framework, each one-on-one learning scenario would allow students to initiate and engage in learning activities individually, specifically accommodating their personal needs, preferences, and learning styles-an individual learning context. Furthermore, peers (including the instructors) may learn and teach bidirectionally via handheld learning devices in various juxtapositions and relationships provided by the shared learning platform-a collaborative learning context. Furthermore, a sense of social presence and engagement with the learning community may be engendered by transforming students’ intragroup participation to intergroup interaction, thus encouraging student readiness to share more experiences in the learning community-a community-based learning context. The current chapter discusses the rationale for and the potential to structure this framework to build a seamless environment for teaching and learning with handhelds.