This Special Issue Reprint studies and reviews the deployment of digital technologies in a range of organizational contexts and highlights the key lessons distilled from recent experience. The papers include studies in the business, healthcare, education and banking sectors, and the technology focus spans artificial intelligence, data mining, blockchain, game theory, and crowd-sourcing techniques. The articles encompass a variety of themes examined in different national contexts, including business start-ups, corporate responsibility, copyright management, public sector expenditure, and sporting performance. The broad span of these articles attests to the increasing relevance and applicability of digitalisation in many aspects of business life and across wider society and highlights the value of assessing the balance of positive and negative impacts as the pace of change continues to accelerate.