Learning from the failure of mechanical systems is a necessity, given that it is the understanding of how and why things fail that generates effective redesign. This subsequently enables the technology that surrounds us to become more reliable, safer, and more economical by extending component life and minimizing the wasteful decisions made to replace systems that am either sound for continued operation could be easily repaired. Considerations for cost-effective decision making, so as to promote healthy machinery, equipment, and structures, are discussed in terms of learning from failure analysis, improving via reliability engineering, and achieving longevity through integrated diagnostics.