Despite substantial financial investments, digital transformation remains elusive for many developing countries. Acknowledging a bias towards developed contexts in existing research, this qualitative study explores the stalled progress of DT in developing countries, exemplified by the case of Haiti. To gain deeper insight into the crucial elements pertinent to DT within this specific context, we conducted interviews with 42 key informants and identified four key roadblocks: Governance structure, resource dependence, organizational readiness, and institutional inertia. Our findings reveal unexpected resistance sources. Unlike prior research, we highlight high-ranking officials themselves as significant impediments to the process, often prioritizing personal gain within dysfunctional and politicized institutions. Additionally, unofficial actors, like lawyers threatened by standardized fees, disrupt progress. Frequent leadership changes and a preference for inefficiency further hinder DT while perpetuating institutional chaos. This study concludes with a research agenda for studying context-specific DT in developing countries.