Retailers play a pivotal role in advancing digital commerce in emerging markets, yet their adoption of digital payment systems remains inconsistent. Drawing on the Technology–Organization–Environment (TOE) framework, this study examines how technologica lreadiness, organizational capability, and environmental influences shape retailers’ adoption behavior in Saudi Arabia. Survey data from retailers in Riyadh indicates that transaction speed, convenience, and perceived usefulness function as key enablers, while transaction fees, limited digital skills, and security concerns act as barriers. Although institutional trust and supportive government initiatives encourage adoption, many retailers remain unaware of formal compliance expectations, illustrating a pattern of compliance without awareness. To account for this dynamic, the TOE framework is extended by incorporating regulatory literacy and institutional trust as contextual dimensions. The study therefore offers theoretical refinement to TOE in policy-driven adoption settings and provides practical implications for improving merchant training, usability support, and regulatory communication to better sustain digital payment usage in emerging digital commerce ecosystems.