In this paper, we introduce the analysis and the design of a new web-based interactive software tool, called WebUbu, which has been developed to serve the undergraduate students' needs related to Linux Operating System (OS) issues. The aim of this software development was twofold: on the one hand to familiarize students with Ubuntu OS environment and, on the other hand to promote the self-learning related to this Linux distribution, in the context of everyday OS classrooms. WbUbu software can be used only for interactive demonstration of features of Linux during lectures and to support instructors for evaluation of students' skills in the lab. For other tasks such as long term studying of Linux-based OS's physical' Linux must be used. Our software is essentially a website that simulates Ubuntu operating system inside a web browser. Undergraduate students can easily explore both graphical user interface (GUI) and command line of Ubuntu's environment. Additionally, students can ascertain the acquired knowledge through an automated examination process and learn from their mistakes as they shown automatically by the software in real time. Educator can manage students' performances that are stored in a database system and assess the individual's cognitive progress resulting from the software contribution. However, WebUbu will give students the chance for practice and self assessment when they not involved in the University's educational process or physical' Linux is unavailable. That software intends to complement the existing teaching and learning methods concerning Operating Systems. (c) 2015 Wiley Periodicals, Inc.