Since the early 1980s, exposure to digital technologies/devices has occurred on a wide cultural/societal level. Numerous writers have posited their impressions of these encounters often times suggesting an ease, comfort, and acceptance on the part of the users, especially those born in 1980 or later. This study examined the ongoing relationship between students from three small colleges and digital technologies through a series of interviews over the span of a year. Students in the study were primarily drawn from majors in education and computer science who were likely to have an ongoing involvement with these technologies/devices on both a professional as well as a personal level. Specific areas of inquiry included the placement of these technologies within their lives as explored through their initial encounters with them, the nature of their ongoing relationship with them, their importance in their lives, and their concerns/hopes for the future with regard to them; the rules of their engagement with them as measured by their engagement levels, how they find meaning in their use, their interactions with intellectual property, and the languages they employ when engaged; their attempts to control/manage them as demonstrated by their understanding of them, their management of these digital devices, the Internet, and their sense of privacy; and their personal representations in the virtual realm on social networking sights and their perception of its influence on them. Discussions about these suggest a community of users that are not entirely at ease, comfortable, or in acceptance of the role these digital technologies/devices play in their lives with some differences noted across generational groups. Much of this appears to be related to the illusions surrounding these digital technologies/devices on the part of the users' with regard to their understanding of them, ability to control/manage them, and knack for assessing the authenticity/genuineness of the messages they are being presented with. Potential courses of action are explored that would mitigate the users' acquiescence to these illusions and provide them with the opportunity to develop the necessary critical literacy skills to better manage them. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]