A number of models exist for deploying digital technologies to enhance student engagement. Many emphasise the centrality of collaborative activities in stimulating engagement, such as Engagement Theory (Kearsley and Shneiderman 1999), Produsage (Bruns 2005) and Participatory Cultures (Jenkins 2006). This paper describes the evaluation of a collaborative technology project entitled EngageME, undertaken in 2009 by Victoria University in partnership with Adult Multicultural Education Services (AMES), and outlines practical steps that educators can take to improve the success of technology-based learning using collaborative strategies. Through a series of technology skills workshops, the EngageME project brought together young at-risk [vocational education and training] VET students and their teachers from adult and community education (ACE) providers in Melbourne and regional Victoria. Workshops consisted of tuition in narrative and storytelling, followed by digital media creation, editing and sharing (video, comics and virtual worlds). For teachers, these workshops provided a new form of professional development and for their students, new skills in media production. Evaluation data were gathered using pre- and post-workshop surveys based on the '2008 E-learning benchmarking survey for teachers' by the Australian Flexible Learning Framework, focus groups, facilitator observations and an online forum. In reflecting on these evaluations, this paper explores the role of technology and collaboration in facilitating and hindering engagement, and provides suggestions on how technology-facilitated engagement can be facilitated in a classroom setting.