This book is based around two key premises: all software is an artefact of human construct and all software shapes the behaviours of those who use it directly or experience its influence indirectly. With the rise of popular consumer-facing generative AI tools, never has understanding these two premises been more important or more obscured. This book explores the relationship between people and software as a relationship between a tool and its users. Through a series of exemplar cases, it presents an examination of the historical development of software from a critical perspective, with special attention given to the consequences of using this software and assumptions made around its neutrality. The author explores the development of the World Wide Web, Word and Excel, and social media, concluding with an investigation of how the principles identified in these earlier examples are now being found within public interface generative AI tools. The book looks beyond the functionality and user interface of the software to look at it as a complex artefact of human manufacture by exploring the wider cultural and technical environment in which the software is created and considering the political, economic and social forces that come to bear on the software and become embodied within. This narrative approach provides readers with valuable insights into the influences of specific software on contemporary society and business, encouraging them to apply a critical lens to their own and their organisation’s software use. This book is a novel read for academics and students within software development, information systems, AI and critical management studies.