The emergence of new information and communication technologies (ICTs) call for new ways of learning and teaching, and integral to this call is new ways of assessing. This chapter provides insights into how ICT offers educators valuable assessment tools with which to more appropriately assess 21st-century lifelong learnerswho increasingly experience learning in digital, networked learning contexts in which learning involves collaboration and constructing new knowledge. This chapter explores how the interests of learning improvement and accountability can be served using online resources, particularly ePortfolios, and how they can be enhanced by the use of Web 2.0 technologies. Issues and insights are provided through an exploration into how ICT can provide valuable assessment tools for diverse stakeholders, including students, parents, administrators and policy officers.