Information Technologies (IT) have gradually transformed into complex digital artefacts with blurred and constantly changing functional boundaries. While this shift offers promising venues that unfold in front of our eyes every day, it also challenges the deeply entrenched knowledge structures on which ordinary users rely to learn about unfamiliar technologies. We propose to take a step back in order to theorize the ambiguous nature of modern IT and to speculate on how users learn to use them. This paper revisits a wide array of management (BYOD, Gamification) and IS design trends (generativity, everyday computing, incompleteness) through the lens of the categorization framework. Our review of the literature on ambiguous products suggests that users exposed to ambiguous technologies may experience a categorization difficulty that disrupts the process of learning how to use them. This difficulty stems from a user’s belief that there are multiple or inconsistent interpretations of why and how to use an IT, as well as a perception that a given IT has some attributes in common with one or several seemingly unrelated ITs. We build on this theorization to propose a research agenda and discuss the expected practical implications of this path of research.

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