This study explores the types of learning profiles that evolve from student use of video annotation software for reflective learning. The data traces from student use of the software were analysed across four undergraduate courses with differing instructional conditions. That is, the use of graded or non-graded self-reflective annotations. Using hierarchical cluster analysis, four profiles of students emerged: minimalists, task-oriented, disenchanted, and intensive users. Students enrolled in one of the courses where grading of the video annotation software was present, were exposed to either another graded course (annotations graded) or non-graded course (annotations not graded) in their following semester of study. Further analysis revealed that in the presence of external factors (i.e., grading), more students fell within the task-oriented and intensive clusters. However, when the external factor is removed, most students exhibited the disenchanted and minimalist learning behaviors. The findings provide insight into how students engage with the different features of a video annotation tool when there are graded or non-graded annotations and, most importantly, that having experience with one course where there are external factors influencing students' use of the tool is not sufficient to sustain their learning behaviour in subsequent courses where the external factor is removed.