Recent technological, cultural and economic factors have shifted the balance between recalling and reconstructing internalised information and accessing externalised information. While digital artefacts constitute an enormous and valuable set of resources, human engagement and reflection are important to the meaningful synthesis and application of knowledge in specific contexts. This is particularly clear in the case of personal photography, where recordings of life events are used to cue not just the facts and details of what happened, but associated subjective, sensory and emotional memory. This article draws on research into personal photography to highlight contrasting drivers of engagement and detachment with digital media, and applies these to students' use of digital media within education. The posing of complex, situated problems that require the use of technology to construct creative, collaborative, multimodal projects is suggested as a way of cultivating social obligation and encouraging selectivity, engagement and reflection with digital media.