As the nature of learning has changed, so too has our notion of literacy. While educators recognize the transformative nature of education in the 21st century, the how and why of assessment still eludes curriculum developers, educational policy-makers and classroom practitioners. Many of the current assessment practices are too narrow, too limited to cater for the oral, critical, linguistic, visual and technological understandings required by today's learners. While teachers are adjusting their pedagogies to match the real-world practice, they are struggling to respond with appropriate assessment techniques. To fully grasp the complexities associated with assessment of these new ways of learning, one must examine the origins, practices and shift to multi modal learning and the impact of this on assessment practices.