This teaching guide, published by the Center for the Advancement of Teaching Excellence at the University of Illinois-Chicago, explores how edtech tools can support authentic assessments and help students develop digital literacy skills. The design of authentic assessments is continuously evolving, especially as students learn in a globally connected and digital world. The teaching guide explores how to incorporate multimedia into lessons and assessments, such as the creation of podcasts, photo and video essays, websites, and social media posts. It provides examples of assignments crafted with assessment authenticity and digital literacy in mind, accompanied by an annotated list of educational software and applications that students may use in classrooms.