In this study, the Big Five factor model of personality traits theory was tested for its ability to predict or explain Employee Information Security Behavior (EISB), when Generational Cohort (GCOHORT) moderated the relationship between the five factors of personality and EISB. The independent variables (IVs) Extraversion, Agreeableness, Conscientiousness, Emotional Stability, and Intellect (EACESI) measured the Big Five factors of personality traits construct, and the dependent variable (DV), File Protection Behavior (FPB), measured the EISB construct. Generational Cohort (GCOHORT) was defined as three age groups, which spanned periods that approximated the generations as follows: 1946-1964 (Baby Boomers), 1965-1980 (Generation X), and 1981-1998 (Millennial). The data were collected by Qualtrics, Inc. according to specific inclusion and exclusion criteria, and respondents were limited to adults 18 years or older who were employed in organizations within the United States. A linear regression model was applied in the study and, in particular, hierarchical linear multiple regression analyses were used to examine whether a statistically significant relationship existed between the IVs and the DV, and whether GCOHORT moderated the relationship between the IVs and the DV. Results indicated that there was a weak correlation between the five factors of personality traits and File Protection Behavior (R = 0.28); nonetheless, there was a statistically significant relationship between the IVs and the DV, and the Big Five factor model of personality traits theory was able to predict File Protection Behavior (p < 0.05). However, when GCOHORT moderated the relationship between EACESI and EISB, there was not a statistically significant relationship between the moderated IVs and the DV (p > 0.05). The major limitation of the study was related to the construction of the online questionnaire and the quality of the data; hence, cautionary advice is offered to mitigate the limitation in future studies. Practical implications cannot be drawn from the results of the study, and results cannot be generalized beyond the sample that was studied. Nevertheless, results indicated that the Big Five factor model of personality traits theory had the ability to predict or explain File Sharing Behavior, though weakly. Recommendations for future research on the phenomenon are offered. [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.]