While no one disputes the good in finding and fixing issues before deploying to production, relying on traditional testing methods in the age of data-intensive, internet scale software has proven to be incomplete. The ability to identify and fix production issues quickly is crucial and requires insight into usage patterns and trends across the entire application architecture. This talk touches on deficiencies of common testing methods, provide real-world examples of discovering odd edge cases with both testing and monitoring, and offers recommendations on metric instrumentation to help companies identify and act on business-affecting problems.