This paper considers the problems surrounding the implementation of road infrastructure plans in a policy perspective. As the main pillar of regional connectivity, road networks provide the link across national markets, foster strong and sustainable economic growth, help meeting people’s basic needs, and promote trade and competiveness. It is argued that planning, implementing, and managing good transportation infrastructures poses a series of challenges that require competence, good governance, and the availability of funds. Such problems become more complex when road projects encompass different states and become transnational. The regional dimension of connectivity involves both opportunities and risks; a cooperative attitude by all parties is viewed as the best ingredient to achieve a positive balance. Since most countries cannot still rely on domestic resources, the paper stresses the role of virtuous policies in directing capital flows from abroad towards the infrastructural projects of Southeast Asia.