We address the pressing need for effective and scalable cybersecurity education methodologies for undergraduate students. While Capture The Flag (CTF) challenges have been instrumental for some learners, for many novices CTF challenges are simply too difficult and too intimidating to be pedagogically effective. By dissecting and individually presenting these concepts through modularized challenges, we introduce a progressive learning curve that allows students to master complex vulnerabilities, even culminating in crafting advanced end-to-end exploits through both userspace and the kernel. Recognizing the learning barriers imposed by debugging and introspection tools, our method uniquely offers self-guiding challenge variants, effectively decoupling problem-solving from tool mastery. Drawing from five years of curating around 400 systems security challenges, this paper details our insights and experiences, emphasizing the pivotal role of an education-first approach over traditional CTFs. Our methodology’s success is underscored by our survey results, with an overwhelming majority of participants acknowledging its pivotal role in deepening their cybersecurity understanding. Furthermore, we have successfully leveraged this material as the foundational content for a follow-on vulnerability research course, where freshly-trained students successfully identified 0-day vulnerabilities in real-world software. As a commitment to global education, we make all challenges and accompanying lecture materials discussed herein freely, and easily, accessible to the world.