The introduction of technical, algorithmically-controlled interactive medial systems into virtually all contexts of everyday life is a relatively recent phenomenon. Implications, for instance, for social and political contexts are still emerging. One probably unexpected but certainly unintended effect is the emergence of gaming the system behaviours. Gaming is seen here as participants taking advantage of systems by interacting with them in unintended ways to gain unjustified benefits. These behaviours are regularly seen as problematic, and measures to prevent or to detect and to react to them are discussed in the academic discourse. This study aims to establish characteristics, practices and causes of such behaviours, exemplatory in the area of interactive, educational tutoring systems. The study is informed by positions from Game Studies, Cognitive Evaluation Theory (CET; Deci, Ryan) and the (post-) phenomenological discourse on the intentionality of non-human actors. It finds that users feel disenfranchised rather than empowered by the intentionality embodied in algorithmic systems; that those systems afford play; and that gaming behaviour can be read as defensive and evasive, rather than aggressive and criminal.