In today’s connected world, there exists a large amount of tools that did not exist during the inception of computing and user interfaces. Many of these have seen their natural advent due to the Internet’s global accessibility. Ever since the initial simple user interfaces of text-based terminals, user testing has been researched and developed thoroughly as it provides a rigid set of feedback to the system architect which can help to more quickly and easily construct a system suited for its purpose. Through various methods of remote usability testing, a teacher-student interface is tested with a set of real users. The results of which are qualitatively compared between themselves and previous results using similar tools and evaluated for their usability. The results indicate that the system that was tested was generally perceived as well-performing but indicated several issues with how the tasks were created, underlining the necessity for a well-documented and thought through approach to the creation of usability testing tasks.