This book explores how digital technologies are transforming cross-border trade in Southeast Asia. It examines IT interoperability within the ASEAN Single Window, a landmark initiative that connects national customs systems to accelerate clearance, strengthen cybersecurity, and enable seamless data exchange. Organized across nine chapters, the book highlights how artificial intelligence, blockchain, cloud computing, and smart connected platforms are reshaping trade flows and regulatory cooperation. Drawing on detailed case studies from Singapore, Malaysia, and Indonesia, it shows how digital innovation reduces transaction costs, shortens clearance times, and empowers small and medium-sized enterprises to participate in regional commerce. Combining theory, policy analysis, and empirical evidence, this book provides both researchers and practitioners with a clear roadmap for advancing digital trade. It is an essential resource for scholars of international trade, policymakers, and business leaders seeking to understand and shape the future of digital transformation in Asia and beyond.