Over the past fourteen years, the authors of this article have collaborated on two community-based participatory action research projects in Appalachian Kentucky. One focused on assessing the social impacts of a major environmental disaster (2000-2014) and the other involves partnering with a small community seeking to transition a struggling, coal-driven economy to a more diverse and sustainable one (2013-present). In what follows, we discuss our experiences working with these Appalachian coalfield communities, which are characterized by low levels of social trust, a situation complicated by negative stereotypes and confused thinking by non-residents about Appalachian coalfield culture. First, we discuss stereotypes of Appalachian culture, among them suspicion and hostility toward "outsiders" and native tendencies toward violence. After debunking the myth that Appalachian culture creates distrust of outsiders, we identify the political economic structures, which have eroded trust in the Central Appalachian coal communities, with particular attention to institutional, structural, and intraregional variation in social trust. Finally, we identify strategies to engage effectively in communities characterized by low levels of trust in government, corporations, and neighbors.