This paper, commissioned by the Mountain Association for Community Economic Development (MACED), explores the relevance of divestment for the Appalachian Transition. The paper provides background on divestment trends as well as insights into the diverse ways that various kinds of investors are approaching fossil-fuel divestment and fossil-free reinvestment. Over the course of this inquiry, which began in late January 2014, we have reached out to nearly three dozen different investors and their advisers, interviewing investment decision-makers from 18 institutions and firms that are grappling with fossil-fuel divestment and are interested in the idea of reinvesting in Appalachia. We focused our outreach primarily on foundations, faith-based investors, financial advisers working with individual clients, and investment consultants and impact investment firms working with institutional investors. Based on this research and outreach, we analyze the potential opportunity that divestment presents for place-based reinvestment into frontline communities in the region. While we found considerable interest in investing in the region to support the transition, numerous obstacles stand in investors’ way. We therefore identify many of the leading obstacles and make several recommendations for overcoming them.