As digital media making becomes increasingly popularized in classrooms, media and arts educators are faced with not only familiarizing digital technologies for curricular planning but also improvising with these unwieldy objects during pedagogical exchanges. Drawing from my five-week action research project, teaching and learning digital art making through digital game modifications, this paper explores the repeated moments of technological breakdowns, failures, and troubles during pedagogical practices through the metaphor of troubleshooting that guided how we framed and approached these troubles. Specifically, I argue that to troubleshoot is to standardize our situated contexts to universal terms, to engage in a relationship premised on the framework of control, and to invest in the temporal order of technological development as predetermined knowledge. As such, I foreground a desire for a different metaphor and turn towards the metaphor of troublecaring to speculate how to respond to the offers of inquiry made by these moments of technological breakdowns, failures, and troubles.