The purpose of this hermeneutic phenomenological study was to explore preservice teachers’ experiences with video observations at Central University. The theory guiding this study was Bandura’s self-efficacy theory as it provides insights into the internal and external factors that affect an individual’s perception of their capabilities. Self-efficacy is a critical component and goal of field experience observations. The central research question for this hermeneutic phenomenological study was: What are preservice teachers’ attitudes and experiences using video annotation software during field experience? The study was divided into two phases: individual interviews with preservice teachers, audio-visual elicitation interviews, a letter-writing activity, and qualitative data aggregation. Four themes were derived from the participants’ experiences: (a) streamlined reflection, (b) digital detachment, (c) the supervisor variable, and (d) program components’ effect on self-efficacy. Interpretations of the themes included four significant interpretations: (a) video annotation software improves reflection capabilities and personal agency, (b) video annotation software is a field supervision tool, not replacement, (c) convenient but not complete: video annotation software asynchronous communication is not enough, and (d) expectations and structure matter.