This chapter explores metaphors used by organizational actors to understand digital transformation and digitalized organizations. Following a “pigeon-holing approach” (Örtenblad 2017), we identify and categorize two sets of metaphors. The first set of metaphors consists of the metaphors of digital transformation: that is, the metaphors that deal with change—the wave metaphor and the digit metaphor. These metaphors help us better understand different dimensions of digital transformation as a technological and organizational change process. The second set consists of the metaphors of digitalized organizations: that is, the metaphors that deal with transformed organizations. Based on Morgan’s (1986) metaphors, the authors identify three root metaphors, namely the machine metaphor, brain metaphor, and instrument of domination metaphor. They argue that using several metaphors as categories helps us identify differences between various phenomena associated with digital transformation and digitalized organizations, and offer an overview of organizational actors’ understandings of these phenomena.