Authenticity is a key to using technology for instruction in ways that enhance learning and support learning transfer. Simply put, a representation is authentic when it shows learners clearly what a task, context, or experience will be like in real practice. More authentic representations help people learn and understand better. They support learning transfer by giving learners an opportunity to see key features and reference points that show when and how tasks need to be done, and how information is relevant to actual task performance. However, designers may need to adjust components of authenticity to optimize initial learning and eventual transfer, depending on the task, learners, and context. This chapter unpacks the concept of authenticity, then discusses and illustrates how considering various elements of authenticity can help designers and trainers make more effective decisions to support learning and development.