With the rapid growth of Facebook, the social networking website is becoming a lucrative target for malicious activity. Users of Facebook therefore should be aware of various malicious attacks and know how to identify them. This research analyzed Facebook users' level of understanding in the domain of malicious social engineering on Facebook. The research examined differences in awareness among multiple generational groups; secondary research questions focused on how factors such as age, gender, education, Internet usage, and trust affected users' awareness of malicious activity. Results suggest that the Baby Boomer generation is the least aware of malicious social engineering tactics on Facebook, specifically in regard to the Donation scam category. In addition, education level and educational background are significantly associated with awareness. These findings indicate a need for future work to gain a deeper understanding of Facebook users' awareness of malicious social engineering and generate targeted training in order to increase said awareness. [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.]