The human component of information systems represents a critical and high-impact target for cyberattacks. Firms address these threats through various means, including security awareness training, security policy monitoring, security controls, and enforcement. Even the most robust technical controls have limits. Consequently, elevating user awareness and integrating user protection within the information system becomes imperative. This study seeks to assess how effectively organizations implement security awareness training to influence user behavior. The assessment examines the impact of security awareness training and security culture on security policy compliance, influenced by leadership directives, and the moderating effect of user comprehension of security tool messaging. Security tools are integral to the larger goal of security compliance. There is limited research examining the relationship between the use of security tools and user intention to comply. This quantitative study utilized purposive snowball sampling via LinkedIn. 106 respondents and 7 incomplete responses were excluded. Analysis on the remaining 99 participants was conducted using Partial Least Square Structural Equation Modeling to test the seven hypotheses. This study contributes to the existing body of knowledge by incorporating employee perceptions of information provided by security tools, enhancing our understanding of factors that shape users' security policy compliance. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]