As computers and the Internet have become integral to daily life, the potential gains from exploiting these resources have increased significantly. The global landscape is now rife with highly skilled wrongdoers seeking to steal from and disrupt society. In order to safeguard society and its infrastructure, a comprehensive approach to research is essential. This work aims to enhance security from three unique viewpoints by expanding the resources available to educators, users, and analysts. For educators, a capture the flag as-a-service was developed to support cybersecurity education. This service minimizes the skill and time needed to establish the infrastructure for hands-on hacking experiences for cybersecurity students. For users, a tool called CloakX was created to improve online anonymity. CloakX prevents the identification of browser extensions by employing both static and dynamic rewriting techniques, thwarting contemporary methods of detecting installed extensions and thus protecting user identity. Lastly, for cybersecurity analysts, a tool named Witcher was developed to automate the process of crawling and exercising web applications while identifying web injection vulnerabilities. Overall, these contributions serve to strengthen security education, bolster privacy protection for users, and facilitate vulnerability discovery for cybersecurity analysts.