This chapter considers the assessment of learning in open, distance, and digital education. To add new insights to the extensive body of relevant prior research literature, the chapter uses two “dimensions” of assessment to summarize and extend this work. The first dimension is assessment function. This includes traditional summative functions (“assessment of learning”), modern formative functions (“for learning”), and contemporary transformative functions (“as learning”). This also includes recently introduced conformative functions (“as compliance”) and deformative functions (“as sabotage”). The second dimension is theory of learning. This includes differential, cognitive-associationist, cognitive-constructivist, and situative/sociocultural theories. This chapter pays particular attention to how these dimensions interact with each other in complex (and often unanticipated) ways, and briefly considers how they interact with two other dimensions (item format and assessment level, as elaborated elsewhere) in open, distance, and digital education.