The Big Five Factors Model (FFM) of personality traits theory was tested for its ability to explain employee information security behavior (EISB), when age, measured by generational cohort (GCOHORT), moderated the relationship between the independent variables (IVs) extraversion, agreeableness, conscientiousness, emotional stability, intellect (EACESI) and the dependent variable (DV), employees’ information security behavior (EISB) which is measured by file protection behavior (FPB). Three age groups defined GCOHORT: 52–70 years old (1946–1964, Baby Boomers), 36–51 yrs old (1965–1980, Generation X), and 18– 35 yrs. Old (1981–1998, Millennial). Results of hierarchical multiple regressions analyses revealed statistically significant relationships between overall personality traits, four individual factors of personality traits, and the DV (p < .05). However, contrary to expectations, GCOHORT did not moderate the relationship between any of the main IVs and the DV (p > .05). Recommendations for future research are offered.