Over the past decade, technological transformation has completely reshaped how companies interact with consumers. Firms now rely extensively on advanced data collection tools, ranging from cookies and online trackers to smart sensors and connected devices in the physical environment. Within this context, companies, governments, and individuals try to come up with their own ways to manage changing dynamics. As a consequence, the extent to which people feel observed may depend on major changes in the environment, regulations imposed by governments, companies’ practices in line with these external factors, and individuals’ personal differences. The first part of this chapter examines the impact of external factors. The second part discusses empirical findings about factors that may vary from person to person as well as identifying concepts that may potentially impact the perception of being observed. Finally, the third part discusses the potential influence of the various types of behaviors people engage in, and how these behaviors themselves may intensify the perception of being observed.