Conflicts among stakeholders are common in Community Informatics (CI) research. They often derive from mismatches of expectations and are exacerbated by communication and intercultural issues. Such mismatches are breaking points that might compromise the relationship of trust among project stakeholders and, ultimately, project outcomes. In CI, reflecting on moments of conflict and mismatch might help researchers attend to assumptions and interpret aspects of the cultural context of the communities they work with, as well as their own. This reflection should, then, contribute to a closer connection among stakeholders and sustainable project outcomes. In this paper, we present the Critical Incidents Analysis (CIA) Framework (Brunello, 2015), a tool that was conceived within the Community and Development Informatics field with the aim to reflect upon incidents and misunderstandings among stakeholders, their different cultural perspectives, and – eventually – deal with project breakdowns. We apply the framework to our own research where we analyse conflicts and mismatches of expectations that arose during the fieldwork conducted by two of the authors. We conclude that the CIA framework, applied “a posteriori” to our cases, was a useful tool to better analyse and report on our research, and to recast incidents as opportunities to enable a deeper understanding and – in some cases – build trust among stakeholders.