Despite growing speculation about the role of human behavior in cyber-security of machines, concrete data-driven analysis and evidence have been lacking. Using Symantec’s WINE platform, we conduct a detailed study of 1.6 million machines over an 8-month period in order to learn the relationship between user behavior and cyber attacks against their personal computers. We classify users into 4 categories (gamers, professionals, software developers, and others, plus a fifth category comprising everyone) and identify a total of 7 features that act as proxies for human behavior. For each of the 35 possible combinations (5 categories times 7 features), we studied the relationship between each of these seven features and one dependent variable, namely the number of attempted malware attacks detected by Symantec on the machine. Our results show that there is a strong relationship between several features and the number of attempted malware attacks. Had these hosts not been protected by Symantec’s anti-virus product or a similar product, they would likely have been infected. Surprisingly, our results show that software developers are more at risk of engaging in risky cyber-behavior than other categories.