Worldwide, the elderly have suffered disproportionately from the effects of the COVID-19 pandemic, both in terms of their prognosis once contracted the disease and in terms of the preventative measures required for this demographic, who are at much higher risk than the rest of the population. In the “new normal”, the well-being of older adults (residing either in their own homes or in care homes) will be ideally monitored remotely. These measures would preserve the independence of individuals without compromising on their safety. In this paper we discuss aspects of the design and implementation of a resident monitoring system (RMS) with particular emphasis on overcoming the barriers for adoption among these populations, by addressing the aspects of usability, privacy and security at the core of the development of such a system. We discuss the current challenges of this research and future work on the RMS.