Driving old, beat-up cars is both a treat and a nightmare, especially when it comes to figuring out why they’ve stopped working (this time). In many ways, diagnosing issues with any old car feels not-at-all dissimilar to monitoring for and diagnosing failures in software. In this talk, I walk through some of the lessons my old junker has taught me about designing monitoring for software in the messy, icky, dammit-I-busted-knuckle-again real-world and how you can apply them to your own apps.