Simplification in IT is an illusion; increasing complexity outpaces every effort to simplify. This episode of the Tech Field Day podcast, recorded on-site at Cloud Field Day 24, features Camberley Bates, Nathan Nielsen, Guy Currier, and Alastair Cooke. Cloud services and centralized management platforms offer simplified interfaces but also introduce a multitude of choices and underlying complexities. History matters; advancements from mainframes to PCs demonstrate continuously shifting goalposts, while the more recent integration of cloud and AI contributes to increased complexity. It may be that AI brings simply advanced simplicity, yet it may also bring the unintended consequence of people becoming "ignorant" of how IT works. CIOs and CTOs need to think strategically to manage increasingly complex environments, striking a balance between patchwork fixes and long-term strategic approaches.