National Instruments (NI), a company that produces automated test equipment and virtual instrumentation software, and PTC, a computer and software technology company, partnered with Tufts University to develop an Internet of Things (IoT) platform for undergraduate engineering students. Through interviews with five engineering students, interviews with two developers of the platform, and usability tests with eight other participants in Tufts University's College of Engineering, I use a gap analysis approach to outline the shortcomings in five aspects of the platform that prevented novice users from quickly developing and/or understanding the IoT data systems. These areas include how students approached the getting started process, using the online dashboard, debugging, adding complexity, and sharing data. Errors, mistakes, and misunderstandings from the usability tests largely revolved around the amount of LabVIEW experience the users had. My analysis suggests future iterations of this toolkit so students can develop solutions more successfully and efficiently.