The increased access to technologies in schools has opened avenues to explore non-traditional styles of teaching and learning. Educational theorists and researchers have long been calling for learnercentered instruction that situates learners in activities that allow them to explore concepts and construct understanding. However, as constructivist theorists and researchers continue to show the benefits of situating learning in meaningful tasks, many barriers still prevent the use of technology-enhanced authentic activities in classrooms (Ertmer, 2005; Shaw, 2003). This chapter aims to analyze the underlying theories of authentic learning and propose methods to support classroom teachers with the design, implementation and assessment of authentic activities.