This paper explores the glitch as a generative problem which is capable of introducing unanticipated possibilities and futures into situations. We understand the glitch as a sociomaterial encounter rather than merely a technical error, and argue that it calls for (re)consideration of here-and-now possible futures through practices of response and repair. Exploring the ways that people seek to respond to glitches, we consider two case studies in which unexpected problems provoke those involved to speculate playfully and practically about new possibilities. In the first case, a malfunctioning ‘Teacherbot’ incites new challenges and pedagogical opportunities in an online learning environment. In the second, Hungarian activists creatively use infrastructural and political problems to make new spaces of protest and to press the government to respond to their concerns. Considering these empirical cases allows us to observe how playful and disruptive dispositions have worked to question the terms of possible futures in the real world, and to unsettle the seemingly given terms of power-relations. Glitches are not a panacea, but they can provide an impetus to act from within situations that are uncertain, and can therefore point to new trajectories and possible futures.