Historical museums and institutions are turning to crowdsourcing initiatives to help collect, organise and preserve information. The systems being deployed are designed with usability and data validity as their primary concern. However, participatory projects also provide an opportunity for institutions to fulfil their ethical remit to engage the public with their digital collections. In this chapter, we (a) place the role of crowdsourcing initiatives in terms of the ethical concerns of cultural heritage institutions and (b) take a preliminary step in theorising experience design concepts to integrate these concerns with crowdsourcing initiatives. We propose that the design of such systems should take into account the experiential qualities of the volunteer’s work. The aim of taking such an approach would be to place more emphasis on these initiatives as participatory processes that are beneficial not only to the institution but also to the individuals taking part. We report a study carried out in collaboration with the American Air Museum, part of the Imperial War Museums in the UK. An image classification system is deployed in gallery to explore participants’ reflections on their user experience and to identify components of engagement that can be targeted for design work. Our findings suggest that a volunteer’s emotional connection to the crowdsourcing content is correlated to their appreciation and enjoyment of the task. We go on to propose a set of design perspectives derived from further analysis of the participants’ qualitative experiences of the task.