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Malicious cybersecurity attacks threaten the confidentiality, integrity, and availability of organizational data. This issue concerns organizational leaders and cybersecurity professionals who must address these threats to prevent operational disruptions, financial losses, reputational damage, and declining stakeholder trust. Grounded in organizational learning theory, the purpose of this qualitative pragmatic inquiry was to explore the strategies information technology security professionals use to proactively respond to evolving cybersecurity threats. The study involved 16 cybersecurity professionals, each with a minimum of five years of experience in implementing both offensive and defensive cybersecurity strategies within their organizations. Data were collected through semistructured interviews and a review of relevant literature. Thematic analysis revealed four major proactive strategies: continuous evaluation and improvement, senior leadership support or buy-in, threat detection and prevention, and training. A key recommendation is to conduct regular and routine risk and threat assessments to monitor and refine an organization’s cybersecurity posture. The implications for positive social change include the potential for organizational leaders and cybersecurity professionals to enhance the security of digital environments, thereby improving public confidence in the protection and exchange of sensitive information via Internet applications.