Video recordings for student teaching field experiences have been utilized with student teachers (also known as teacher candidates) to (a) capture the demonstration of their lesson plans, (b) critique their abilities within the performance, and (c) share and rate experiences for internal and external evaluations by the state and other organizations. Many times, the recording, saving, grading, and sharing process was not efficient. Thus, the feedback cycle from the university supervisor to the teacher candidate was negatively impacted. However, one communication technology tool that has the potential to facilitate the feedback process is video annotation software. This communication technology uses the storage within a remote server, known also as a cloud, to store videos that include typed commentary that is in sync with the portion of the video recorded. A group of university supervisors piloted a video annotation tool during student teaching to rate its effectiveness. Through a survey, the participants addressed how they perceived the implementation of the video annotation tool within the student teaching experience. Results suggest a video annotated technology-based supervision method is feasible and effective if paired with effective training and technical support.