Web 2.0 technologies are very familiar to students who represent the group called the “millennials” in this society due to their birthdates. They are noted for their technological savvy and their ability to use new information and communication technologies without reservation. With this in mind, teacher educators who utilize culturally relevant practices modified a traditional practice of one-dimensional videotaping to support the proficiencies of the participating teacher candidates. The tool used to support traditional video recording was a video annotation software tool that allows the reviewer to type comments in synchronization with the viewed portion of a recording. This video annotation tool allowed the teacher candidates to: a) record their lessons via a smartphone application, b) invite their university supervisor to watch in real-time, c) send a link of the university's media storage location via a built-in compression tool, as well as d) receive text feedback/annotations from their university supervisor within the recording that was in synchronization with the reviewed behavior. Overall, teacher candidates saw the video annotation tool as an effective tool to support collaborations with their university supervisor. Challenges such as storage limitations on smart phones and sound quality are discussed as well as other possible implications in this pilot study.