The theme of technological breakdown, error, failure, or malfunction has, in a certain way, always been present in the history of the philosophy of technology. From Heidegger’s hammer to contemporary discussion of algorithmic bias, technological failure has been seen as revealing of something, as a means to obtain knowledge about technology or the world. For example, Verbeek (2004, p. 79) discusses the breaking down of a computer, pointing out how it is no longer a transparent tool to be used without any awareness; instead, the tool becomes opaque and “abruptly demands interaction with itself.” In this paper, I draw on the concept of exemplary situations to explicate and problematize some of the features of understanding technological failure in the philosophy of technology. In her book about how the practices related to eating may help to rethink philosophical categories such as being or knowing, Mol uses the term exemplary situations as a method to grasp how “philosophical texts become easier to understand if we dig out the empirical incidents that inform them” (Mol, 2021, p. 18). These empirical incidents can be explicitly presented in the form of examples or implicitly manifested as a background against which philosophical theorizing happens. In this talk, by reading some canonical texts in the philosophy of technology through the prism of their exemplary situations, I show how through these exemplary situations, i.e., explicit examples or implicit context, technological failure is rendered as individual, experiential, frictionless, and perceived through the position of a user or an observer. While acknowledging their analytical value, I seek to problematize these features by showing how technological failure can instead be collective, political, full of frictions, and perceived from the position of someone upon whom the technological failure enacts harm. Seen this way, failure plays not only an epistemological function, making us question what can be learned from mistakes. More than that, failure engenders its form of politics, making us think of who is learning from such failures and at whose expense. I explicate this alternative understanding of technological failure by interpreting certain controversies around facial recognition.