This article deals with fieldwork in challenging research contexts that make preparation for field research particularly difficult. Challenging contexts include generally insecure places, politicized contexts, and unknown settings. Drawing on our experience in the field, we discuss four challenges that are common across these contexts: access, positionality, researcher well-being, and research design and data collection. Bringing together insights from fieldwork with urban elites and in the countryside, this paper describes problems that occurred in both settings and identifies a set of interpersonal skills that helped the authors to tackle the challenges of the field and seize the opportunities it offered. This article posits that recognizing the importance of certain interpersonal skills, namely: openness, empathy, humility, and flexibility, precedes the identification of practical tools. Interpersonal skills, instead, focus on a general attitude that underlies researchers’ capacity to make informed choices about specific courses of actions, preparing fieldworkers to be prepared to confront problems once they arise.