This article highlights the importance of rethinking literacy assessment in a digital and global world. Although pressures currently abound to narrow conceptions and practices of literacy, especially in an era of high stakes testing, digital multimodality and connectivity offer the potential for new ways of thinking, representing, and communicating, as well as new avenues for participating in relationships across social, geographic, and cultural difference. We explore the challenges of redesigning assessments so that they better take into account children's multiliterate capabilities. In so doing, we offer examples from our work in afterschool contexts that demonstrate how we have grappled with the complexities of assessment in new times. (Contains 3 footnotes.)