Background: It would be easy to think the technological shifts in the digital revolution are simple incremental progressions in societal advancement. However, the nature of digital technology is resulting in qualitative differences in nearly all parts of daily life. Purpose: This paper investigates how the new possibilities for understanding, exploring, simulating, and recording activity in the world open possibilities for rethinking assessment and learning activities. Research Design: This analytic essay enumerates three changes to assessment likely to result from the ability to gather data from every day learning activities. Findings: The digital revolution allows us to use technology to extend human abilities, represent the world, and collect and store data in previously unavailable ways, all opening new possibilities for the unobtrusive ubiquitous assessment of learning. This is a dramatic shift from previous eras in which physical collection of data was often obtrusive and likely to cause reactive effects when inserted into daily activity. These shifts have important implications for assessment theory and practice and the potential to transform how we ultimately make inferences about students. Conclusions/Recommendations: The emerging universality of digital tasks and contexts in the home, workplace, and educational environments will drive changes in assessment. We can think about natural integrated activities rather than decontextualized items, connected social people rather than isolated individuals, and the integration of information gathering into the process of teaching and learning, rather than as a separate isolated event. As the digital instrumentation needed for educational assessment increasingly becomes part of our natural educational, occupational, and social activity, the need for intrusive assessment practices that conflict with learning activities diminishes.