This chapter explores some of the technological elements that will greatly enhance user interaction with personal photos on mobile devices in the near future. It reviews major technological innovations that have taken place in recent years which are contributing to reshaping people’s personal photo management behaviour and thus their needs, and presents an overview of the major design issues in supporting these for mobile access. It then introduces the currently very active research area of content-based image analysis and context-awareness. These technologies are becoming an important factor in improving mobile interaction by assisting automatic annotation and organisation of photos, thus reducing the chore of manual input on mobile devices. Considering the pace of the rapid increases in the number of digital photos stored on our digital cameras, camera phones and online photoware sites, the authors believe that the subsequent benefits from this line of research will become a crucial factor in helping to design efficient and satisfying mobile interfaces for personal photo management systems.