The purpose of this quantitative inferential study is to determine the level of correlation between the organizational factors of information security awareness, balanced security processes, and organizational structure with the size of the estimation gap of information security implementations mediated by the end user intentionality. The study used structural equations modeling (SEM) to assess the goodness of fit of the proposed model with the information technology executives and professionals of the government of the Commonwealth of Puerto Rico. The SEM analysis confirmed a very good fit of the proposed model with the sample data from the target population. The model provided the information to confirm the significant correlations between the organizational factors with the user intentionality factor, and between the user intentionality and the size of the estimation gap. Also, the study confirmed a partial mediating role of the user intentionality between the organizational factors and the size of the estimation gap. The study offers recommendations to governmental executives about a way to lower the estimation gap on information security implementation projects. [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.]