The rapid ageing of the population is a worldwide inexorable demographic transformation. At a time of immense social, political and economic change, the growing elderly population is at the forefront of global burden, placing an increasing strain on the federal, state, and local budgets. Many public policy responses to the impending ageing epidemic have begun, particularly with regards to dementia prevention and quality of life for older adults. However, to date, the fruition of such efforts remains to be discovered. Indeed, there is a need to find more novel and multifaceted ways of understanding the fragmentary changes and underlying mechanisms in the biopsychosocial contexts of ageing. Discovering better ways to measure these intricate domains will create better insight into how to improve clinical and public health information systems for the development of more personalisation support and services across the continuum of aged care. Technology now permeates all aspects of our everyday living. Digital footprints are data arising as a by-product of interactions we do as part of everyday living. The digital traces we live behind, be it on internet, social media, on mobile phone apps, as well as in health records (EHRs) could be used to infer how we behave and interact with environment, and how we feel in different situations. Commercial sector has very successfully used these footprints in the advertisement and marketing space. This type of information may provide clinicians with an unobtrusive way of monitoring older adults in their daily living, and provide an alternative means to traditional self-report and expert-rated assessment. In this paper we present two innovative digital footprint applications, Actionable Intime Insights and the SAIL Mobile app, which aim to facilitate "Ageing in Place" through adaptive, dynamic, early intervention strategies. These systems are devised to unveil contextual indicators of how a person is functioning mentally, socially, behaviourally and physically in their own environment, as to as assist those with chronic conditions better self-manage by facilitating assistance with care and medication needs just in time.