<p class="ETSNormal">Annotation of video for learning provides tertiary education students with the opportunity to view and engage with course material in an active rather than passive-receptive mode. This multiple-case study examined the integration of a media annotation tool, <em>MAT</em>, across four vocational programs in a Melbourne university. <em>MAT</em> was integrated to allow students to access, interact with, and learn from a range of video-based learning materials. Within one audiovisual technology and three property services cohorts, the teachers planned for and implemented <em>MAT</em> to allow students to analyse case-based and role-played scenarios to help develop workplace skills. This paper frames these integrations within ‘Prepare-Participate-Connect’ models, and illustrates that while students were in the main satisfied with their learning experiences, learning design contexts (such as video choice, individual versus team analysis, and timing of intervention) affected student satisfaction. Analysis of the data indicates that additional to participation, preparation and connection are key to student satisfaction when annotating video.</p>