Systems that are technically secure may still be exploited if users behave in unsafe ways. Most studies of user behavior are in controlled laboratory settings or in large-scale between-subjects measurements in the field. Both methods have shortcomings: lab experiments are not in natural environments and therefore may not accurately capture real world behaviors (i.e., low ecological validity), whereas large-scale measurement studies do not allow the researchers to probe user intent or gather explanatory data for observed behaviors, and they offer limited control for confounding factors. The SBO addresses the gap through a panel of participants consenting to our observing their daily computing behavior in situ, so we can understand what constitutes “insecure” behavior. We use the security behavior observatory to attempt to answer a number of research questions, including 1) What are risk indicators of a user’s propensity to be infected by malware?  2) Why do victims fail to update vulnerable software in a timely manner? 3) How can user behavior be modeled with respect to security and privacy “in the wild”?