This article reports on the findings of a study that investigated the effects of instructional conditions and prior experience on students' self-reflection. The study was conducted with the use of a video annotation tool that was used by undergraduate performing arts students to reflect on their video-recorded performances. The study shows a consistent positive effect of previous experience with the video annotation tool for engagement with reflection. Graded instructional conditions with feedback had a positive effect on increasing higher order reflections particularly for students with prior experience with the video annotation tool for reflective purposes. The finding suggests that when including reflection in the curriculum, it is important to consider introducing it at a program or degree level rather than individual courses in order to provide an opportunity for students to gain experience with reflection and any particular tool that is used (e.g., a video annotation tool). Furthermore, reflective tasks should be scaffolded into the curriculum with ample opportunity for formative feedback and summative assessment in order to encourage higher order thinking and foster students' metacognitive awareness and monitoring for increased goal-setting and acknowledgement of the motive or effect of their observed behavior.