Student engagement in the online learning environment is critical for academic success. One increasingly popular means through which to facilitate this engagement is the use of web-conferencing software. While there are a variety of potential applications, this paper will evaluate the use of one such web-conferencing tool to support synchronous online class meetings. Challenges integrating live sessions into an online academic and career skills class will be discussed, including the logistic challenges of a synchronous online meeting, the limitations of the synchronous platform (GoToMeeting), and the alignment of technical support to issues for both instructors and students. Considerations for future online synchronous instructions will also be proffered.