Computers are problem-solving tools at heart. Without an operating system though, they would be rendered useless. Most computer users are unaware of the inherent capabilities of the bare OS and the problems it can solve for them. This comes naturally in an era of commercialized solutions in the form of apps and software packages. However, gaining understanding of the built-in functions of an OS hidden behind the graphical user interface may let students discover new, personally relevant problems. In turn, attempts at formulating and solving these could help students gain complex cognitive skills in IT. This study explores the notion of problem-posing and proposes a Web-based learning environment; where users may create guides and tutorials in addition to posing their own educational problems pertaining to GNU/Linux Command Line use. Problems are stored in a repository and may be rated, reviewed, discussed or solved by peers. A virtual environment running a Linux distribution may be configured by users to accompany a posed problem and help create a complete sandbox reflecting the problem's story and structural elements.