Environmental scanning (ES) improves managerial decisions by linking the business environment with the organization’s internal capabilities. This chapter provides an overview of current developments in ES, underscoring the link between the managerial decision-making process and the different modes of scanning both internal and external information sources, particularly the World Wide Web (WWW). The psychological foundations of human ES activities are scrutinized, and cutting-edge technologies that support monitoring or even scanning of autonomous information sources are discussed to integrate both aspects in a holistic perspective on ES. We identify the most serious challenge in ES to be the detection of relevant sources in vast information environments. Based on the Information Foraging Theory (IFT), we propose an innovative approach to assessing the information gain offered by digitally available sources.