The most complicated IT environments I’ve worked in weren’t built that way on purpose. They got there through a sequence of reasonable decisions made by reasonable people under real pressure. The problem comes later, when twenty years of reasonable decisions turn into an environment no one has fully stepped back to understand. The ones carrying the most complexity aren’t usually the ones that made the worst decisions. They’re the ones that grew the fastest, had the most demands on their IT teams or operated in environments where buying was distributed across business units.