The use of Linux based Operating Systems (OS) in the classroom is increasing, but there is little research to address usability differences between Windows and Linux based OSs. Moreover, studies related to the ability for students to navigate effectively between Ubuntu 14.04 Long Term Support (LTS) and Windows 8 OSs are scant. This research aims to bridge the gap between modern Linux and Windows Oss, as the former represents a viable alternative to eliminate licensing costs for educational institutions. Preliminary findings, based on the analysis of the System Usability Scale results from a sample of 14 students, demonstrated that Ubuntu users did not require technical support to use the system, while the majority found little inconsistency in the system and regarded it as well integrated.