This paper presents the design of an application for engagement with audiovisual digital cultural heritage in the classroom, called the Carrot. The aim of this interactive tool is to make online cultural heritage accessible and understandable for students in different levels of education. In relation to this work we pose two research questions: Why do we need to develop tools for contextualization of audiovisual cultural heritage? And: How do we design anddevelop such tools? The preliminary answers to these questions come from our experiences in the design process, which deepened our understanding of a tool in the context of the classroom. We then relate this to the digital humanities project, EUscreenXL. Initial conclusions suggest that tools for contextualization of audiovisual cultural heritage can engage students with cultural heritage, develop digital media literacy, and support contemporary didactics. These tools need to be developed across platforms, using nonproprietary software and involving a multidisciplinary group of experts.