In today’s “cloudy with a chance of outages" world, it is as important as ever to effectively monitor systems and their internals. Modern tools and platforms like Docker and Pivotal Cloud Foundry give our infrastructure greater flexibility and utility than ever before. But these tools are as susceptible—and in many cases more susceptible—to having fundamental problems of capacity, overutilization, and stability. In this talk, Rob Desjarlais explores the tools that Liberty Mutual uses to monitor their systems, from vmstat, iostat, and ss (Socket State) to Datadog and more. These tools have helped Liberty Mutual understand how their systems and applications scale as their business grows to new heights.