For lifelogging, or the recording of one’s life history through digital means, to be successful, a range of separate multimodal mobile devices must be employed. These include smartphones such as the N95, the Microsoft SenseCam – a wearable passive photo capture device, or wearable biometric devices. Each collects a facet of the bigger picture, through, for example, personal digital photos, mobile messages and documents access history, but unfortunately, they operate independently and unaware of each other. This creates significant challenges for the practical application of these devices, the use and integration of their data and their operation by a user. In this chapter, authors discuss the software engineering challenges and their implications for individuals working on integration of data from multiple ubiquitous mobile devices drawing on experiences working with such technology over the past several years for the development of integrated personal lifelogs. The chapter serves as an engineering guide to those considering working in the domain of lifelogging and more generally to those working with multiple multimodal devices and integration of their data.