This document discusses technical debt and when it is appropriate to declare "technical bankruptcy". It provides definitions and examples of technical debt, technical inflation, and technical bankruptcy. Technical bankruptcy occurs when debt is accumulating faster than it can be cleared, the time to clear debt would be longer than reimplementing from scratch, or sustainable resources to clear debt are unavailable. The document then discusses strategies for addressing technical debt, including auditing the current system, creating a refactoring plan, deciding whether to start over or use new tools, and provides a case study of technical debt with the SUMO support system.