We employ knowledge regarding the early phases of system trespassing events and develop a context-related, theoretically driven study that explores computer networks’ social vulnerabilities to remote system trespassing events. Drawing on the routine activities perspective, we raise hypotheses regarding the role of victim client computers in determining the geographical origins and temporal trends of (1) successful password cracking attempts and (2) system trespassing incidents. We test our hypotheses by analyzing data collected from large sets of target computers, built for the sole purpose of being attacked, that were deployed in two independent research sites (China and Israel). Our findings have significant implications for cyber-criminological theory and research.