The rapid development of information and communication technologies (ICT) has significantly changed the ways today’s children entertain, socialize, and learn. The digital society in the twenty-first century requires a complete suite of cognitive and psychological abilities and perspectives that enable the individual to intelligently consume and creatively develop digital products, and ethically participate and lead in a world that has become increasingly mediated by technology. How can today’s education help our students develop technological competencies that they will need to survive and thrive in the twenty-first century? In this chapter, we address this question by envisioning school assessments that focus on digital technology proficiencies. Our discussion centers on the question “What are the most critical skills students need to equip with in terms of digital technologies?” Specifically, this chapter reviews the role of digital technologies in the twenty-first century, examines what technology proficiency is necessary for students to fully participate in the society, discusses how the concept and standards of digital proficiency have evolved in the last a few decades, and then investigates how student digital technology proficiency has been assessed and discusses what schools need to do to prepare their students with proficient digital literacy.