A critical production bug triggered an investigation that revealed something unexpected: our accidental complexity had grown far beyond the essential complexity of the system. In this talk, we share lessons learned from analyzing how this happened and the sociotechnical dynamics behind it. We uncovered unclear boundaries, fragmented ownership, and systemic loops that rewarded heroics instead of flow. By applying Lean principles and value-stream mapping, we identified waste and bottlenecks that had been invisible for months. With Team Topologies and Domain-Driven Design, we exposed hidden dependencies, reduced cognitive load, and clarified ownership. We’ll distinguish technical debt from accidental complexity, illustrate the real cases uncovered during the investigation, and show how redesigning team interactions helped rebalance the system and move the project toward simplification and sustainable flow.