Although succession is the single most important issue in family-owned businesses (FOBs), there is scarce comprehensive and integrative analysis of the context (i.e., the social, organizational, and normative setting) where succession events occur. Research usually focuses on the success or failure of succession processes, instead of the risks faced by FOBs during succession. The succession process takes time and multiple actors are involved. Therefore, succession is influenced by uncertainty and unforeseen events. This study addresses the aforementioned gap in the literature by investigating how context can reduce the risk of failure in succession. Based on organizational change theory and the resource-based view, this study considers family and business circumstances where interactions between actors take place and succession occurs. Since the research goal is deeply embedded in context, this paper presents a comparative case study of three Spanish FOBs that have experienced different kinds of organizational change in relation to management succession. The main conclusion is that risk of succession failure depends not only on detailed process design and planning, but also on a well-developed firm and family context that provides sufficient familiness resources to cope with unexpected events and address conflicts.