Learning Linux typically demands initial setup overhead, creating a paradox where newcomers must already somewhat understand Linux environments to effectively learn about them. To address this challenge, we developed an online interactive learning curriculum explicitly designed to eliminate the barrier of manual setup. Our approach divides core Linux concepts into small, focused challenges, enabling incremental mastery through active practice. Beyond traditional exercises, we introduce intentionally playful and even destructive scenarios, such as compromising security, deploying forkbombs, and executing “doomsday” commands like rm -rf / to solidify understanding through memorable experiences. These “shenanigan” challenges not only reinforce technical skills but instill the system consequences of mismanagement, highlighting the flexibility, power, and potential pitfalls of Linux environments in an engaging, experiential manner.